Research Progress on Sultine

doi:10.6023/A23100435

Abstract

Heterocycles are a highly valuable class of complex scaffolds that are involved in a various kind of well-known organic compounds of industrial and pharmacological importance. Sultine, an important class of sulfur-containing heterocyclic compounds, plays central roles in medicine, biology and material science. The sulfur atom in sultine is located at a vertex of a stable pyramid without identical substituents, making it a chiral center with potential applications in asymmetric synthesis. The asymmetry of sultine can be easily eliminated by oxidizing it into sultone. In addition, sultines have shown to be versatile intermediates in organic synthesis. They can act as useful synthons with hidden bifunctionality: opening the heterocycle at the S—O bond leads to the simultaneous appearance of two functional groups in the product. Despite their potential, the chemical research of sultines have been long neglected and underdeveloped due to their inaccessibility. Only recently, some research groups have discovered protocols for the preparation of these heterocycles and explored their properties using methods such as visible light-induced radical homolytic substitution cyclization and radical polar crossover cyclization, and so on. It is worth noting that although sultines have been discussed in a few reviews, they are not systematic but very fragmentary. Owing to the increasing interest in studies on sultines and their transformations. The synthesis methods, physical properties and applications of sultines are systematically summarized in the past 130 years. The synthetic tactics are reviewed by highlighting their product diversity, selectivity and applicability, along with the mechanistic rationale where possible. Additionally, the chemical transformations of sultines, including photolysis, thermolysis, ring-opening reactions, oxidation/reduction reactions, and rearrangement reactions, are demonstrated. The usefulness of sultines in synthesis, medicine and materials is described as well. Finally, the development status of sultine compounds is reviewed, and a future perspective is provided, in order to offer reference for researchers engaged in sultine chemistry.

Key words: sultine, synthesis, property, application

Cite this article

Lingyue Yang, Yunting Li, Chao Shu. Research Progress on Sultine[J]. Acta Chimica Sinica, 2024, 82(2): 171-189.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 64

Figure 1. Sultine chemistry

Figure 2. Rongalite involved the synthesis of sultines

Figure 3. Anion relay cyclization of dihalogen-o-xylene

Figure 4. DBU-mediated nucleophilic substitution cyclization

Figure 5. Nucleophilic substitution cyclization for the synthesis of sultine B and D

Figure 6. Cyclization of hydroxysulfinates to sultine

Figure 7. Cyclization of hydroxysulfoxides to sultine

Figure 8. Synthesis of α,β-unsaturated γ-sultine

Figure 9. Synthesis of α,β-unsaturated γ-sultine from propargyl alcohol

Figure 10. Electrophilic cyclization on unsaturated bonds

Figure 11. Friedel-Crafts cyclization

Figure 12. Synthesis of benzo-fused sultine

Figure 13. Synthesis of γ-sultine by radical homolytic substitution

Figure 14. Photocatalyzed synthesis of benzo-fused sultines

Figure 15. Proposed mechanism of photocatalysed synthesis of benzo-fused sultines

Figure 16. Photocatalyzed synthesis of fluoromethylated sultines

Figure 17. Proposed reaction mechanism of fluoromethylated sultine

Figure 18. Synthesis of polycyclic sultine

Figure 19. Energy transfer powered synthesis of sultines

Figure 20. Proposed mechanism of energy transfer catalysis

Figure 21. Synthesis of dibromo substituted sultine

Figure 22. Electrocatalyzed synthesis of sultines

Figure 23. Synthesis of sultine via radical rearrangement

Figure 24. Synthesis of sultine via oxidation

Figure 25. Synthesis of sultine by m-CPBA oxidation

Figure 26. Synthesis of sultine by NaIO4 oxidation

Figure 27. Synthesis of sultine via LiAlH4 reduction

Figure 28. β-Sultone reduction

Figure 29. Synthesis of sultine by ring expansion

Figure 30. Synthesis of sultine by ring expansion under base conditions

Figure 31. Synthesis of sultine by contraction

Figure 32. Synthesis of sultine by rearrangement

Figure 33. Synthesis of sultine B by rearrangement

Figure 34. SO2 involved cycloaddition-1

Figure 35. SO2 involved cycloaddition-2

Figure 36. SO2 involved cycloaddition-2

Figure 37. The synthesis of sultines via other methods-1

Figure 38. Chloranil involved the synthesis of sultines

Figure 39. Synthesis of benzo-fused sultine B

Figure 40. The synthesis of sultines via other methods-2

Figure 41. X-ray crystallography analysis

Figure 42. Configuration analysis of sultine

Figure 43. Mono-olefin mediated Diels-Alder cycloaddition reaction

Figure 44. 1,3-Butadiene mediated Diels-Alder cycloaddition reaction

Figure 45. Decomposition of β-sultine

Figure 46. Thermolysis of β,γ-unsaturated sultine

Figure 47. Decomposition of cyclopropane fused sultine

Figure 48. Thermolysis of dibenzoxathiine oxide A

Figure 49. Thermolysis of benzofused sultine A

Figure 50. Photolytic decomposition of the sultine A and E

Figure 51. UV light photolysis of sultine

Figure 52. Thermolysis and photolysis of sultine A

Figure 53. Photolytic decomposition of δ-sultine

Figure 54. Alkaline hydrolysis of sultine

Figure 55. Cleavage of sultines by halide ions

Figure 56. Alcoholysis of β-sultine

Figure 57. Organometallic reagents involved ring opening reactions

Figure 58. Oxidation of sultines

Figure 59. Reduction reactions of sultines

Figure 60. Rearrangement of sultine

Figure 61. Application of sultine-1

Figure 62. Application of sultine-2

Figure 63. Application of sultine-3

Figure 64. Application of sultine-4

References 148

[1]	Zhang, Y.; Li, H.; Yang, X.; Zhou, P.; Shu, C. Chem. Commun. 2023, 59, 6272. doi: 10.1039/D3CC01238G
[2]	Bondarenko, O. B.; Saginava, L. G.; Zyk, N. V. Russ. Chem. Rev. 1996, 65, 147. doi: 10.1070/RC1996v065n02ABEH000204
[3]	Dittmer, D. C.; Hoey, M. D. In The Chemistry of Sulphinic Acids, Esters and their Derivatives, Chapter 9, Ed.: Patai, S., Wiley, Chichester, England, 1990, p. 239.
[4]	Zhu, Z.; Deng, Z.; Ouyang, X.; Shu, C. Synlett 2023, 34, 1943. doi: 10.1055/a-2080-5069
[5]	Jarvis, W. F.; Hoey, M. D.; Finocchio, A. L.; Dittmer, D. C. J. Org. Chem. 1988, 53, 5750. doi: 10.1021/jo00259a026
[6]	Baker, W.; Pant, C. M.; Stoodley, R. J. J. Chem. Soc., 1978, 668.
[7]	Knittel, D. Monatsh. Chem. 1982, 113, 37. doi: 10.1007/BF00814334
[8]	Harpp, D. N.; Gleason, J. G. Tetrahedron Lett. 1969, 1447.
[9]	Harpp, D. N.; Gleason, J. G.; As, D. K. J. Org. Chem. 1971, 36, 322. doi: 10.1021/jo00801a017
[10]	Harpp, D. N.; Gleason, J. G. J. Org. Chem. 1971, 36, 1314. doi: 10.1021/jo00808a038
[11]	Inoue, H.; lnoguchi, N.; Imoto, E. Bull. Chem. Soc. Jpn. 1977, 50, 197. doi: 10.1246/bcsj.50.197
[12]	Gaoni, Y. J. Org. Chem. 1981, 46, 4502. doi: 10.1021/jo00335a037
[13]	Hoey, M. D.; Dittmer, D. C. J. Org. Chem. 1991, 56, 1947. doi: 10.1021/jo00005a054
[14]	Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. Jr. J. Am. Chem. Soc. 2000, 122, 10991. doi: 10.1021/ja002340q
[15]	Schmibt, A. H.; Kircher, G.; Willems, M. J. Org. Chem. 2000, 65, 2379. doi: 10.1021/jo9915877
[16]	Kotha, S.; Ganesh, T.; Ghost, A. K. Bioorg. Med. Chem. Lett. 2000, 10, 1755. pmid: 10937741
[17]	Wu, A.-T.; Liu, W.-D.; Chung, W.-S. J. Chin. Chem. Soc. (Taipei) 2002, 49, 77.
[18]	Kotha, S.; Khedkar, P. J. Org. Chem. 2009, 74, 5667. doi: 10.1021/jo900658z
[19]	Jia, J. Z.; Scarborough, R. M.; Zhang, P.; Halfon, S.; Arfsten, A. E.; Sinha, U.; Zhu, B.-Y. Chem. Pharm. Bull. 2009, 57, 1004. doi: 10.1248/cpb.57.1004
[20]	Meng, X.; Zhang, W.; Tan, Z.; Du, C.; Li, C.; Bo, Z.; Li, Y.; Yang, X.; Zhen, M.; Jiang, F.; Zheng, J.; Wang, T.; Jiang, L.; Shu, C.; Wang, C. Chem. Commun. 2012, 48, 425. doi: 10.1039/C1CC15508C
[21]	Meng, X.; Zhang, W.; Tan, Z.; Li, Y.; Ma, Y.; Wang, T.; Shu, C.; Wang, C. Adv. Funct. Mater. 2012, 22, 2187. doi: 10.1002/adfm.v22.10
[22]	Smith, G. M. T.; Burton, P. M.; Bray, C. D. Angew. Chem., Int. Ed. 2015, 54, 15236. doi: 10.1002/anie.v54.50
[23]	Charlton, J. L.; Durst, T. Tetrahedron Lett. 1984, 25, 5287.
[24]	Durst, T.; Charlton, J. L.; Mount, D. B. Can. J. Chem. 1986, 64, 246. doi: 10.1139/v86-042
[25]	Jung, F.; Molin, M.; Van Den Elzen, R.; Durst, T. J. Am. Chem. Soc. 1974, 63, 935.
[26]	Sharma, N. K.; de Reinach-Hirtzbach, F.; Durst, T. Can. J. Chem. 1976, 54, 3012. doi: 10.1139/v76-427
[27]	Breau, L.; Sharma, N. K.; Butler, J. R.; Durst, T. Can. J. Chem. 1991, 69, 185. doi: 10.1139/v91-029
[28]	Malwal, S. R.; Gudem, M.; Hazra, A.; Chakrapani, H. Org. Lett. 2013, 15, 1116. doi: 10.1021/ol400190f
[29]	Malwal, S. R.; Chakrapani, H. Org. Biomol. Chem. 2015, 13, 2399. doi: 10.1039/C4OB02466D
[30]	Thoumazean, E.; Jousseaume, B.; Tiffon, F.; Durboudin, J.-G. Heterocycles 1982, 19, 2247. doi: 10.3987/R-1982-12-2247
[31]	Von Rein, F. W.; Richey, H. G. J. Organomet. Chem. 1969, 20, 32.
[32]	Eisch, J. J.; Merkley, J. H. J. Organomet. Chem. 1969, 20, 27.
[33]	Welker, M. E. Chem. Rev. 1992, 92, 97. doi: 10.1021/cr00009a004
[34]	Scott, E. E.; Donnelly, E. T.; Welker, M. E. J. Organomet. Chem. 2003, 673, 67. doi: 10.1016/S0022-328X(03)00167-0
[35]	Franks, M. A.; Schrader, E. A.; Pietsch, E. C.; Pennella, D. R.; Torti, S. V.; Welker, M. E. Bioorg. Med. Chem. 2005, 13, 2221. doi: 10.1016/j.bmc.2004.12.037
[36]	Ying, M.; Smentek, M. G.; Ma, R.; Day, C. S.; Torti, S. V.; Welker, M. E. Lett. Org. Chem. 2009, 6, 242. doi: 10.2174/157017809787893064
[37]	Wang, M.; Jiang, X. Chem. Rec. 2021, 21, 3338. doi: 10.1002/tcr.v21.12
[38]	Zeng, D.; Wang, M.; Deng, W.-P.; Jiang, X. Org. Chem. Front. 2020, 7, 3956. doi: 10.1039/D0QO00987C
[39]	Smil, D. V.; Souza, F. E. S.; Fallis, A. G. Bioorg. Med. Chem. Lett. 2005, 15, 2057. doi: 10.1016/j.bmcl.2005.02.056
[40]	Dhami, K. S. Chem. Ind. (London) 1968, 1004.
[41]	Dhami, K. S. Indian J. Chem. 1974, 12, 278.
[42]	Henrick, K.; Johnson, B. L. Aust. J. Chem. 1972, 25, 2263.
[43]	Torosyan, M. A.; Mirzoyan, R. S.; Isakhanyan, S. S.; Arutyunyan, A. M. Arm. Khim. Zh. 1986, 39, 124(Chem. Abstr. 1987, 106, 138299).
[44]	Barbieri, W.; Bernardi, L.; Coda, S.; Vigevani, A. Tetrahedron Lett. 1971, 4913.
[45]	Hanson, G.; Kemp, D. S. J. Org. Chem. 1981, 46, 5441. doi: 10.1021/jo00339a048
[46]	Coulomb, J.; Certal, V.; Fensterbank, L.; Lacôte, E.; Malacria, M. Angew. Chem., Int. Ed. 2006, 45, 633. doi: 10.1002/anie.v45:4
[47]	Kyne, S. H.; Aitken, H. M.; Schiesser, C.; Lacôte, E.; Malacria, M.; Ollivier, C.; Fensterbank, L. Org. Biomol. Chem. 2011, 9, 3331. doi: 10.1039/c1ob05043e
[48]	Aiken, H. M.; Hancock, A. N.; Schiesser, C. H. Chem. Commun. 2012, 48, 8326. doi: 10.1039/c2cc33856d
[49]	Coulomb, J.; Certal, V.; Larraufie, M.-H.; Ollivier, C.; Corbet, J.-P.; Mignani, G.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. - Eur. J. 2009, 15, 10225. doi: 10.1002/chem.v15:39
[50]	Salaverri, A. F. N.; Maestro, M. C.; Alemán, J. Org. Lett. 2019, 21, 5295. doi: 10.1021/acs.orglett.9b01911
[51]	Pitzer, L.; Schwarz, J. L.; Glorius, F. Chem. Sci. 2019, 10, 8285. doi: 10.1039/c9sc03359a pmid: 32055300
[52]	Wiles, R. J.; Molander, G. A. Isr. J. Chem. 2020, 60, 281. doi: 10.1002/ijch.v60.3-4
[53]	Sharma, S.; Singh, J.; Sharma, A. Adv. Synth. Catal. 2021, 363, 3146. doi: 10.1002/adsc.v363.13
[54]	Li, H.; Zhang, Y.; Yang, X.; Deng, Z.; Zhu, Z.; Zhou, P.; Ouyang, X.; Yuan, Y.; Chen, X.; Yang, L.; Liu, M.; Shu, C. Angew. Chem., Int. Ed. 2023, 62, e202300159.
[55]	Zhang, Y.; Zhou, P.; Yang, X.; Li, H.; Deng, Z.; Ren, M.; Shu, C. Adv. Synth. Catal. 2023, 365, 3478. doi: 10.1002/adsc.v365.20
[56]	Deng, Z.; Zhu, Z.; Ru, Z.; Zou, X.; Ouyang, X.; Yang, X.; Zhou, P.; Tian, S.; Ma, X.; Song, R.; Sun, Q.; Lin, C.; Shu, C. ACS Catal. 2023, 13, 13232. doi: 10.1021/acscatal.3c03367
[57]	Kelley, C. J.; Carmack, M. Tetrahedron Lett. 1975, 16, 3605. doi: 10.1016/S0040-4039(00)91335-2
[58]	Knittel, D.; Kastening, B. J. Appl. Electrochem. 1973, 3, 291. doi: 10.1007/BF00613035
[59]	Kastening, B.; Gostisa-Mihelcic, B. J. Electroanal. Chem. 1979, 100, 801. doi: 10.1016/S0022-0728(79)80199-0
[60]	Knittel, D. Monatsch. Chem. 1982, 113, 37. doi: 10.1007/BF00814334
[61]	Dittmer, D. C.; Henion, R. S.; Takashina, N. J. Org. Chem. 1969, 34, 1310. doi: 10.1021/jo01257a023
[62]	Astrologes, G. W.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 4390. doi: 10.1021/ja00455a030
[63]	Davis, A. P.; Whitham, G. H. J. Chem. Soc. Chem. Commun. 1981, 741.
[64]	Block, E.; Wall, A. J. Org. Chem. 1987, 52, 809. doi: 10.1021/jo00381a020
[65]	Wolinsky, J.; Marhenke, R. L. J. Org. Chem. 1975, 40, 1766. doi: 10.1021/jo00900a019
[66]	Kohn, H.; Charumilind, P.; Simonsen, S. H. J. Am. Chem. Soc. 1979, 101, 5431. doi: 10.1021/ja00512a062
[67]	Kohn, H.; Charumilind, P. J. Org. Chem. 1980, 45, 4359. doi: 10.1021/jo01310a019
[68]	Martin, L. D.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 3511. doi: 10.1021/ja00452a059
[69]	Astrologes, G. W.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 4400. doi: 10.1021/ja00455a031
[70]	Nishio, T.; Shiwa, K.; Sakamoto, M. Helv. Chim. Acta 2002, 85, 2383. doi: 10.1002/1522-2675(200208)85:8【-逻辑与-】amp;lt;2383::AID-HLCA2383【-逻辑与-】amp;gt;3.0.CO;2-E
[71]	Kawęcki, R. Tetrahedron: Asymmetry 2003, 14, 2827.
[72]	Wolinsky, J.; Marhenke, R. L. J. Org. Chem. 1975, 40, 1766. doi: 10.1021/jo00900a019
[73]	Peters, R.; Koch, F. M. Synlett 2008, 1505.
[74]	Peters, R.; Koch, F. M. Chem. - Eur. J. 2011, 17, 3679. doi: 10.1002/chem.v17.13
[75]	Hoffmann, R. W.; Sieber, W. Justus Liebigs Ann. Chem. 1967, 703, 96. doi: 10.1002/jlac.v703:1
[76]	Dittmer, D. C.; Henion, R. S.; Takashina, N. 153rd National Meeting, American Chemical Society, Miami, Florida, 1967, Abstract O-101.
[77]	Dittmer, D. C.; Henion, R. S.; Takashina, N. J. Org. Chem. 1969, 34, 1310. doi: 10.1021/jo01257a023
[78]	Christl, M.; Brunn, E.; Lanzendorfer, F. J. Am. Chem. Soc. 1984, 106, 373. doi: 10.1021/ja00314a022
[79]	King, J. F.; Piers, K.; Piers, D. J. H.; Mc lntosh, C.; de Mayo, P. J. Chem. Soc., Chem. Commun. 1969, 31, 34.
[80]	King, J. F.; de Mayo, P.; McIntosh, C. L.; Piers, K.; Smith, D. J. H. Can. J. Chem. 1970, 48, 3704. doi: 10.1139/v70-619
[81]	Dittmer, D. C.; Nelsen, T. R. J. Org. Chem. 1976, 41, 3044. doi: 10.1021/jo00880a033
[82]	Hall, C. R.; Smith, D. J. H. Tetrahedron Lett. 1974, 3633.
[83]	Schuckmann, H. P.; Von Sonntag, C. J. Photochem. 1983, 22, 55. doi: 10.1016/0047-2670(93)80008-D
[84]	Dodson, R. M.; Hammen, P. D.; Davis, R. A. J. Chem. Soc., Chem. Commun. 1968, 9.
[85]	Dodson, R. M.; Hammen, P. D.; Davis, R. A. J. Org. Chem. 1971, 36, 2693. doi: 10.1021/jo00817a026
[86]	Dodson, R. M.; Hammen, P. D.; Fan, J. Y. J. Org. Chem. 1971, 36, 2703. doi: 10.1021/jo00817a028
[87]	King, J. F.; Huston, B. L.; Hawson, A.; Komery, J.; Deaken, D. M.; Harding, D. R. K. Can. J. Chem. 1971, 49, 936. doi: 10.1139/v71-153
[88]	King, J. F.; Hawson, A.; Huston, B. L.; Danks, L. J.; Komery, J. Can. J. Chem. 1971, 49, 943. doi: 10.1139/v71-154
[89]	King, J. F.; Hawson, A.; Deaken, D. M.; Komery, J. J. Chem. Soc., Chem. Commun. 1969, 33.
[90]	Kowalewski, R.; Margarethe, P. Angew. Chem., Int. Ed. 1988, 27, 1374.
[91]	Harpp, D. N.; Steliou, K.; Chan, T. H. J. Am. Chem. Soc. 1978, 100, 1222. doi: 10.1021/ja00472a032
[92]	Harpp, D. N.; Mullins, D. F. Can. J. Chem. 1983, 1, 757.
[93]	Heldeweg, R.; Hogeveen, H. J. Am. Chem. Soc. 1976, 98, 2341. doi: 10.1021/ja00424a060
[94]	Durst, T.; Tetreault-Ryan, L. Tetrahedron Lett. 1978, 2353.
[95]	De Lucchi, O.; Lucchini, V. J. Chem. Soc., Chem. Commun. 1982, 464.
[96]	Hogeveen, H.; Zwart, L. J. Am. Chem. Soc. 1982, 104, 4889. doi: 10.1021/ja00382a024
[97]	Cutler, A.; Fish, R. W.; Giering, W. P.; Rosenblum, M. J. Am. Chem. Soc. 1972, 94, 4354. doi: 10.1021/ja00767a060
[98]	Shabarov, Y. S.; Saginova, L. G.; Bondarenko, O. B. USSR SU 1209694 1986[Chem. Abstr. 1987, 106, p. 5002].
[99]	Saginova, L. G.; Bondarenko, O. B.; Shabarov, Y. S. J. Org. Chem. USSR, 1985, 21, 608.
[100]	Bondarenko, O. B.; Voevodskaya, T. I.; Saginova, L. G.; Tafeenko, V. A.; Shabarov, Y. S. J. Org. Chem. USSR 1987, 23, 1736.
[101]	Bohen, J. M.; Joullie, M. M. Tetrahedron Lett. 1971, 1815.
[102]	Bohen, J. M.; Joullie, M. M. J. Org. Chem. 1973, 38, 2652. doi: 10.1021/jo00955a017
[103]	Gruetzmacher, H.; Roesky, H. W. Chem. Ber. 1987, 120, 995. doi: 10.1002/cber.v120:6
[104]	Lichtenberg, D. W.; Wojcicki. A. J. Organomet. Chem. 1971, 33, C77. doi: 10.1016/S0022-328X(00)87408-2
[105]	Haszeldine, R. N.; Bannister, W. D.; Booth, B. L.; Loader, P. L. J. Chem. Soc. A 1971, 930.
[106]	Thomasson, J. E.; Robinson, P. W.; Ross, D. A.; Wojcicki, A. Inorg. Chem. 1971, 10, 2130. doi: 10.1021/ic50104a008
[107]	Kroll, J. O.; Wojcicki, A. J. Organomet. Chem. 1974, 66, 95. doi: 10.1016/S0022-328X(00)93892-0
[108]	Churchill, M. R.; Wormald, J.; Ross, D. A.; Thomasson, J. E.; Wojcicki, A. J. Am. Chem. Soc. 1970, 92, 1795. doi: 10.1021/ja00709a082
[109]	Braverman, S.; Reisman, D. J. Am. Chem. Soc. 1977, 99, 605. doi: 10.1021/ja00444a048
[110]	Braverman, S.; Reisman, D. Tetrahedron Lett. 1977, 1753.
[111]	Braverman, S.; Duar, Y. J. Am. Chem. Soc. 1983, 105, 1061. doi: 10.1021/ja00342a073
[112]	Veselovskaya, S. V.; Saginova, L. G.; Shabarov, Y. S. J. Org. Chem. USSR 1987, 23, 115.
[113]	Strating, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1967, 86, 641. doi: 10.1002/recl.v86:6
[114]	Bonini, B. F.; Maccagnani, G.; Mazzanti, G.; Thijs, L.; Ambrosius, H. P. M. M.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1977, 1468.
[115]	Bonini, B. F.; Maccagnani, G.; Mazzanti, G.; Pedrini, P.; Zwanenburg, B. Gazz. Chim. Ital. 1977, 107, 283.
[116]	Gaillard, S.; Papamicaël, C.; Dupas, G.; Marsais, F.; Levacher, V. Tetrahedron 2005, 61, 8138. doi: 10.1016/j.tet.2005.06.047
[117]	Givens, E. N.; Hamilton, L. A. J. Org. Chem. 1967, 32, 2857. doi: 10.1021/jo01284a045
[118]	Liskamp, R. M. J.; Zeegers, H. J. M.; Ottenheijm, H. C. J. J. Org. Chem. 1981, 46, 5408. doi: 10.1021/jo00339a034
[119]	Xi, Z.; Cheng, X.-F.; Chen, W.-B.; Cao, L.-Q. Tetrahedron Lett. 2006, 47, 3337. doi: 10.1016/j.tetlet.2006.03.089
[120]	Marson, C. M.; Giles, P. R. J. Org. Chem. 1995, 60, 8067. doi: 10.1021/jo00129a056
[121]	Haasnoot, C. A. G.; Liskamp, R. M. J.; van Dael, P. A. W.; Noordik, J. H.; Ottenheijm, H. C. J. J. Am. Chem. Soc. 1983, 105, 5406. doi: 10.1021/ja00354a037
[122]	Buchanan, G. W.; Sharma, N. K.; de Reinach-Hirtzbach, F.; Durst, T. Can. J. Chem. 1977, 55, 44. doi: 10.1139/v77-008
[123]	Markovic, D.; Roversi, E.; Scoppelliti, R.; Vogel, P; Meana, R.; Sordo, J. A. Chem. Eur. J. 2003, 9, 4911. doi: 10.1002/chem.v9:20
[124]	Roversi, E.; Scopelliti, R.; Solari, E.; Vogel, P.; Braa, P.; Menndez, B.; Sordo, J. A. Chem. Eur. J. 2002, 8, 1336. doi: 10.1002/(ISSN)1521-3765
[125]	Roversi, E.; Vogel, P. Helv. Chim. Acta 2002, 85, 761. doi: 10.1002/1522-2675(200203)85:3【-逻辑与-】amp;lt;761::AID-HLCA761【-逻辑与-】amp;gt;3.0.CO;2-Q
[126]	Jung, F.; Sharma, N. K.; Durst, T. J. Am. Chem. Soc. 1973, 95, 3420. doi: 10.1021/ja00791a078
[127]	Nokami, J.; Kunieda, N.; Kinoshita, M. Tetrahedron Lett. 1975, 16, 2179. doi: 10.1016/S0040-4039(00)72671-2
[128]	Durst, T.; Gimbarzevsky, B. P. J. Chem. Soc., Chem. Commun. 1975, 724.
[129]	Jung, F.; Molin, M.; Van Den Elzen, R.; Durst, T. J. Am. Chem. Soc. 1974, 63, 935.
[130]	Jung, F. J. Chem. Soc., Chem. Commun. 1976, 525.
[131]	Squires, T. G.; Venier, C. G.; Hodgson, B. A.; Chang, L. W.; Davis, F. A.; Panunto, T. W. J. Org. Chem. 1981, 46, 2373. doi: 10.1021/jo00324a031
[132]	Durst, T.; Finlay, J. D.; Smith, D. J. H. J. Chem. Soc., Perkin Trans. 1 1979, 1950.
[133]	Durst, T.; Huang, J. C.; Sharma, N. K. Can. J. Chem. 1978, 56, 512. doi: 10.1139/v78-082
[134]	Burger, U.; Gmunder, C.; Schmidlin, S.; Bernardinelli, G. Helv. Chim. Acta 1990, 73, 1724. doi: 10.1002/hlca.v73:6
[135]	King, J. F.; Mayo, P. D.; McIntosh, C. L.; Piers, K.; Smith, D. J. H. Can. J. Chem. 1970, 48, 3704. doi: 10.1139/v70-619
[136]	Harpp, D. N.; Vines, S. M.; Montillier, J. P.; Chan, T. H. J. Org. Chem. 1976, 41, 3987. doi: 10.1021/jo00887a012
[137]	Duboudin, J. G.; Jousseaume, B.; Thoumazeau, E. Bull. Soc. Chim. Fr. 1983, 105.
[138]	Xi, Z.; Cheng, X.-F.; Chen, W.-B.; Cao, L.-Q. Tetrahedron Lett. 2006, 47, 3337. doi: 10.1016/j.tetlet.2006.03.089
[139]	Givens, E. N.; Hamilton, L. A. J. Org. Chem. 1967, 32, 2857. doi: 10.1021/jo01284a045
[140]	Henrick, K.; Johnson, B. L. Aust. J. Chem. 1972, 25, 2263. doi: 10.1071/CH9722263
[141]	Chan, T. H.; Montillier, J. P.; van Horn, W. F.; Harpp, D. N. J. Am. Chem. Soc. 1970, 92, 7224. doi: 10.1021/ja00727a048
[142]	Dondoni, A.; Giorgianni, P.; Battaglia, A.; Andreetti, G. D. J. Chem. Soc., Chem. Commun. 1981, 350.
[143]	Torelli, V.; Philbert, D. Chem. Abstr. 1978, 89, 110126.
[144]	Torelli, V.; Philbert, D. Chem. Abstr. 1980, 93, 26659.
[145]	Yolka, S.; Dunach, E.; Loiseau, M.; Lizzani-Cuvelier, L.; Fellous, R.; Rochard, S.; Schippa, C.; George, G. Flavour Fragrance J. 2002, 17, 425. doi: 10.1002/ffj.v17:6
[146]	Pirkle, W. H.; Hoekstra, M. S. J. Am. Chem. Soc. 1976, 98, 1832. doi: 10.1021/ja00423a031
[147]	Ngamnithiporn, A.; Chuentragool, P.; Ploypradith, P.; Ruchirawat, S. Org. Lett. 2022, 24, 4192. doi: 10.1021/acs.orglett.2c01437
[148]	Katritzky, A. R.; Zhang, Z. Z.; Lang, H.; Jubran, N.; Leichter, L. M.; Sweeny, N. J. Mater. Chem. 1997, 57, 1399.

亚磺酸内酯研究进展