REVIEWS

Advances in Deallylation

  • Yu Wang ,
  • Jingyang Wang ,
  • Xiaoyu Wu ,
  • Guangni Ding ,
  • Zhaoguo Zhang ,
  • Xiaomin Xie
Expand
  • a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
    b School of Materials Science and Engineering, Nanchang University, Nanchang 330031
* Corresponding authors. E-mail: ;

Received date: 2020-09-13

  Revised date: 2020-10-28

  Online published: 2020-11-19

Supported by

National Natural Science Foundation of China(21672143); Interdisciplinary Program of Shanghai Jiao Tong University(YG2017MS26)

Abstract

Allyl groups, as a kind of universal protective groups in organic synthesis, are easily introduced, and stable under acidic, basic and reductive conditions. Moreover, the deallylation may occur efficiently and selectively under mild conditions. Therefore, functional group protection with allyl moiety plays a significant role in organic synthesis, especially in the synthesis of natural products and pharmaceutical industry. In recent decades, various methods of deallylation have been developed. Herein, the comprehensive development on the deallylation reaction with base and reductant, oxidation and free radical, Lewis-acid, iodine, transition metals, and electrochemical methods is reviewed.

Cite this article

Yu Wang , Jingyang Wang , Xiaoyu Wu , Guangni Ding , Zhaoguo Zhang , Xiaomin Xie . Advances in Deallylation[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1337 -1358 . DOI: 10.6023/cjoc202009031

References

[1]
Greene, T.W.; Wuts, P.G. M., Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons, Inc., New York, 1999.
[2]
(a) Weissman, S.A.; Zewge, D. Tetrahedron 2005, 61,7833.
[2]
(b) Tang, J.-Y.; Liu, H.-X.; Huang, C.-S. Technol. Dev. Chem. Ind. 2016, 45,15. (in Chinese)
[2]
( 唐剑耀, 刘红星, 黄初升, 化学技术与开发, 2016, 45,15.)
[2]
(c) Li, Z.J.; Zhang, S.Q.; Wang, A.B.; Cai, M.S. Acta Chim. Sinica 1998, 56,1128. (in Chinese)
[2]
( 李中军, 张三奇, 王安邦, 蔡孟深, 化学学报, 1998, 56,1128.)
[2]
(d) Zhou, Y.; Zhang, L.R.; Zhang, L.H. Acta Chim. Sinica 2001, 59,1691. (in Chinese)
[2]
( 周英, 张亮仁, 张礼和, 化学学报, 2001, 59,1691.)
[2]
(e) Deng, X.; Liu, W.; Li, C.; Zhang, Z.; Wang, X.; Liu, J. Chin. J. Org. Chem. 2011, 31,75. (in Chinese)
[2]
( 邓喜玲, 刘卫东, 李超, 张志丽, 王孝伟, 刘俊义, 有机化学, 2011, 31,75.)
[3]
(a) Zhang, L.; Wang, Y.; Yu, J.; Zhang, G.; Cai, X.; Wu, Y.; Wang, L. Tetrahedron Lett. 2013, 54,4019.
[3]
(b) Takagi, K.; Fukuda, H.; Shuto, S.; Otaka, A.; Arisawa, M. Adv. Synth. Catal. 2015, 357,2119.
[3]
(c) Bu, X.; Williams, M.; Jo, J.; Koide, K.; Welch, C.J. Chem. Commun. 2017, 53,720.
[4]
Prosser, T.J. J. Am. Chem. Soc. 1961, 83,1701.
[5]
Price, C.C.; Snyder, W.H. J. Am. Chem. Soc. 1961, 83,1773.
[6]
(a) Oltvoort, J.J.; Kloosterman, M.; van Boom, J.H. Recl. Trav. Chim. Pays-Bas 1983, 102,501.
[6]
(b) Guibe, F.; M'Leux, Y.S. Tetrahedron Lett. 1981, 22,3591.
[7]
Gevorgyan, V.; Yamamoto, Y. Tetrahedron Lett. 1995, 36,7765.
[8]
Nicolaou, K.C.; Caulfield, T.J.; Kataoka, H.; Stylianides, N.A. J. Am. Chem. Soc. 1990, 112,3693.
[9]
Gigg, R.; Warren, C.D. J. Chem. Soc. C 1968,1903.
[10]
Halkes, K.M.; Slaghek, T.M.; Vermeer, H.J.; Kamerling, J.P.; Vliegenthart, J.F. G. Tetrahedron Lett. 1995, 36,6137.
[11]
Mereyala, H.B.; Lingannagaru, S.R. Tetrahedron 1997, 53,17501.
[12]
Cunningham, J.; Gigg, R.; Warren, C.D. Tetrahedron Lett. 1964, 5,1191.
[13]
(a) Gigg, J.; Gigg, R. J. Chem. Soc. C 1966,82.
[13]
(b) Smith, A.B.; Rivero, R.A.; Hale, K.J.; Vaccaro, H.A. J. Am. Chem. Soc. 1991, 113,2092.
[14]
Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116,7919.
[15]
Lamberth, C.; Bednarski, M.D. Tetrahedron Lett. 1991, 32,7369.
[16]
Pirrung, F.O. H.; Rutjes, F. P., J.T.; Hiemstra, H.; Speckamp, W.N. Tetrahedron Lett. 1990, 31,5365.
[17]
Effenberger, F.; J?ger, J. J. Org. Chem. 1997, 62,3867.
[18]
Kametani, T.; Huang, S.-P.; Ihara, M.; Fukumoto, K. J. Org. Chem. 1976, 41,2545.
[19]
Thomas, R.M.; Mohan, G.H.; Iyengar, D.S. Tetrahedron Lett. 1997, 38,4721.
[20]
Li, C.B.; Ji, X.J.; Zhang, S.M.; Lu, M.; Zhao, Z.X.; Cui, Y.; Xu, Y.L.; Yang, Q.C.; Zhang, W.Q. Chin. Chem. Lett. 2003, 14,459.
[21]
Pawar, B.V.; Lokhande, P.D. Synth. Commun. 2009, 39,2445.
[22]
Mann, F.G.; Pragnell, M.J. J. Chem. Soc. 1965,4120.
[23]
Bailey, W.F.; England, M.D.; Mealy, M.J.; Thongsornkleeb, C.; Teng, L. Org. Lett. 2000, 2,489.
[24]
Sanz, R.; Martinez, A.; Marcos, C.; Fananas, F.J. Synlett 2008,1957.
[25]
Alonso, E.; Ramón, D.J.; Yus, M. Tetrahedron 1997, 53,14355.
[26]
Kariyone, K.; Yazawa, H. Tetrahedron Lett. 1970, 11,2885.
[27]
Choudary, B.M.; Prasad, A.D.; Swapna, V.; Valli, V.L. K.; Bhuma, V. Tetrahedron 1992, 48,953.
[28]
Yadav, J.S.; Chandrasekhar, S.; Sumithra, G.; Kache, R. Tetrahedron Lett. 1996, 37,6603.
[29]
Kumar, P.; Cherian, S.K.; Jain, R.; Show, K. Tetrahedron Lett. 2014, 55,7172.
[30]
Robles, Diaz, R.; Rodriguez Melgarejo, C.; Plaza Lopez-Espinosa, M.T.; Izquierdo Cubero, I. J. Org. Chem. 1994, 59,7928.
[31]
Yang, S.G.; Park, M.Y.; Kim, Y.H. Synlett 2002,492.
[32]
Dahlen, A.; Sundgren, A.; Lahmann, M.; Oscarson, S.; Hilmersson, G. Org. Lett. 2003, 5,4085.
[33]
Escoubet, S.; Gastaldi, S.; Timokhin, V.I.; Ber-trand, M.P.; Siri, D. J. Am. Chem. Soc. 2004, 126,12343.
[34]
Perchyonok, V.T.; Ryan, S.J.; Langford, S.J.; Hearn, M.T.; Tuck, K.L. Synlett 2008,1233.
[35]
Balgotra, S.; Venkateswarlu, V.; Vishwakarma, R.A.; Sawant, S.D. Tetrahedron Lett. 2015, 56,4289.
[36]
Garbers, C.F.; Steenkamp, J.A.; Visagie, H.E. Tetrahedron Lett. 1975, 16,3753.
[37]
Bhatt, M.V.; El-Morey, S.S. Synthesis 1982,1048.
[38]
Akiyama, T.; Hirofuji, H.; Ozaki, S. Tetrahedron Lett. 1991, 32,1321.
[39]
Sakate, S.S.; Kamble, S.B.; Chikate, R.C.; Rode, C.V. New J. Chem. 2017, 41,4943.
[40]
Nagaraju, M.; Krishnaiah, A.; Mereyala, H.B. Synth. Commun. 2007, 37,2467.
[41]
(a) Konda, S.G.; Humne, V.T.; Lokhande, P.D. Green Chem. 2011, 13,2354.
[41]
(b) Humne, V.T.; Hasanzadeh, K.; Lokhande, P.D. Res. Chem. Intermed. 2013, 39,585.
[41]
(c) Humne, V.; Lokahnde, P. Synth. Commun. 2014, 44,929.
[42]
Patil, A.M.; Kamble, D.A.; Lokhande, P.D. ChemistrySelect 2017, 2,8418.
[43]
Satyanarayana, K.; Chidambaram, N.; Chandra-sekaran, S. Synth. Commun. 1989, 19,2159.
[44]
Kadam, S.M.; Nayak, S.K.; Banerji, A. Tetrahedron Lett. 1992, 33,5129.
[45]
Talukdar, S.; Nayak, S.K.; Banerji, A. J. Org. Chem. 1998, 63,4925.
[46]
Lee, J.; Cha, J.K. Tetrahedron Lett. 1996, 37,3663.
[47]
Ohkubo, M.; Mochizuki, S.; Sano, T.; Kawaguchi, Y.; Okamoto, S. Org. Lett. 2007, 9,773.
[48]
Rajakumar, P.; Murali, V. Synth. Commun. 2003, 33,3891.
[49]
Ito, H.; Taguchi, T.; Hanzawa, Y. J. Org. Chem. 1993, 58,774.
[50]
Corey, E.J.; Suggs, J.W. J. Org. Chem. 1973, 38,3224.
[51]
(a) Gent, P.A.; Gigg, R. J. Chem. Soc., hem. Commun. 1974,277.
[51]
(b) Gigg, R. J. Chem. Soc., erkin Trans. 1 1980,738.
[52]
Sundberg, R.J.; Hamilton, G.S.; Laurino, J.P. J. Org. Chem. 1988, 53,976.
[53]
Ziegler, F.E.; Brown, E.G.; Sobolov, S.B. J. Org. Chem. 1990, 55,3691.
[54]
Zacuto, M.J.; Xu, F. J. Org. Chem. 2007, 72,6298.
[55]
Boss, R.; Scheffold, R. Angew. Chem., nt. Ed. 1976, 15,558.
[56]
Mori, M.; Ban, Y. Chem. Pharm. Bull. 1976, 24,1992.
[57]
Bieg, T.; Szeja, W. J. Carbohydr. Chem. 1985, 4,441.
[58]
Nakayama, K.; Uoto, K.; Higashi, K.; Soga, T.; Kusama, T. Chem. Pharm. Bull. 1992, 40,1718.
[59]
Mereyala, H.B.; Guntha, S. Tetrahedron Lett. 1993, 34,6929.
[60]
Honda, M.; Morita, H.; Nagakura, I. J. Org. Chem. 1997, 62,8932.
[61]
(a) Ishizaki, M.; Yamada, M.; Watanabe, S.-I.; Hoshino, O.; Nishitani, K.; Hayashida, M.; Tanaka, A.; Hara, H. Tetrahedron 2004, 60,7973.
[61]
(b) Yamada, M.; Watanabe, S.-I.; Hoshino, O.; Ishizaki, M.; Hayashida, M.; Tanaka, A.; Hara, H. Chem. Pharm. Bull. 2003, 51,1220.
[62]
(a) Hata, G.; Takahashi, K.; Miyake, A. J. Chem. Soc., hem. Commun. 1970,1392.
[62]
(b) Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45,230.
[63]
Jeffrey, P.D.; McCombie, S.W. J. Org. Chem. 1982, 47,587.
[64]
Kunz, H.; Unverzagt, C. Angew. Chem., nt. Ed. 1984, 23,436.
[65]
Minami, I.; Ohashi, Y.; Shimizu, I.; Tsuji, J. Tetrahedron Lett. 1985, 26,2449.
[66]
(a) Four, P.; Guibe, F. Tetrahedron Lett. 1982, 23,1825.
[66]
(b) Dangles, O.; Guibé, F.; Balavoine, G.; Lavielle, S.; Marquet, A. J. Org. Chem. 1987, 52,4984.
[67]
Roos, E.C.; Bernabe, P.; Hiemstra, H.; Speckamp, W.N.; Kaptein, B.; Boesten, W.H. J. J. Org. Chem. 1995, 60,1733.
[68]
Deziel, R. Tetrahedron Lett. 1987, 28,4371.
[69]
Yamada, T.; Goto, K.; Mitsuda, Y.; Tsuji, J. Tetrahedron Lett. 1987, 28,4557.
[70]
Garro-Helion, F.; Merzouk, A.; Guibé, F. J. Org. Chem. 1993, 58,6109.
[71]
(a) Beugelmans, R.; Bourdet, S.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35,4349.
[71]
(b) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1995, 36,3129.
[72]
Lemaire-Audoire, S.; Savignac, M.; Genêt, J.P.; Bernard, J.-M. Tetrahedron Lett. 1995, 36,1267.
[73]
(a) Genêt, J.P.; Blart, E.; Savignac, M.; Lemeune, S.; Paris, J.-M. Tetrahedron Lett. 1993, 34,4189.
[73]
(b) Lemaire-Audoire, S.; Savignac, M.; Blart, E.; Pourcelot, G.; Genêt, J.P.; Bernard, J.-M. Tetrahedron Lett. 1994, 35,8783.
[73]
(c) Genêt, J.P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Paris, J.-M.; Bernard, J.-M. Tetrahedron 1994, 50,497.
[73]
(d) Lemaire-Audoire, S.; Savignac, M.; Pourcelot, G.; Genet, J.-P.; Bernard, J.-M. J. Mol. Catal. A: Chem. 1997, 116,247.
[74]
Seki, M.; Kondo, K.; Kuroda, T.; Yamanaka, T.; Iwasaki, T. Synlett 1995,609.
[75]
Murakami, H.; Minami, T.; Ozawa, F. J. Org. Chem. 2004, 69,4482.
[76]
Mora, G.; Piechaczyk, O.; Le Goff, X.F.; Le Floch, P. Organometallics 2008, 27,2565.
[77]
Mao, Y.; Liu, Y.; Hu, Y.; Wang, L.; Zhang, S.; Wang, W. ACS Catal. 2018, 8,3016.
[78]
Enugala, R.; Carvalho, L.C. R.; Marques, M.M. B. Synlett 2010,2711.
[79]
Martínez-Calvo, M.; Couceiro, J.R.; Destito, P.; Rodríguez, J.; Mosquera, J.; Mascare?as, J.L. ACS Catal. 2018,8.
[80]
Garner, A.L.; Song, F.; Koide, K. J. Am. Chem. Soc. 2009, 131,5163.
[81]
Nieberding, M.; Tracey, M.P.; Koide, K. ACS Sens. 2017, 2,1737.
[82]
Jbara, M.; Eid, E.; Brik, A. Org. Biomol. Chem. 2018, 16,4061.
[83]
Alcaide, B.; Almendros, P.; Alonso, J.M. Chem.-Eur. J. 2003, 9,5793.
[84]
Alcaide, B.; Almendros, P.; Alonso, J.M. Chem.-Eur. J. 2006, 12,2874.
[85]
Tanaka, S.; Saburi, H.; Ishibashi, Y.; Kitamura, M. Org. Lett. 2004, 6,1873.
[86]
Tanaka, S.; Saburi, H.; Kitamura, M. Adv. Synth. Catal. 2006, 348,375.
[87]
Tanaka, S.; Saburi, H.; Murase, T.; Yoshimura, M.; Kitamura, M. J. Org. Chem. 2006, 71,4682.
[88]
Cadierno, V.; Garcia-Garrido, S.E.; Gimeno, J.; Nebra, N. Chem. Commun. 2005,4086.
[89]
Kamijo, S.; Huo, Z.; Jin, T.; Kanazawa, C.; Yamamoto, Y. J. Org. Chem. 2005, 70,6389.
[90]
Kajihara, K.; Arisawa, M.; Shuto, S. J. Org. Chem. 2008, 73,9494.
[91]
Sasmal, P.K.; Carregal-Romero, S.; Parak, W.J.; Meggers, E. Organometallics 2012, 31,5968.
[92]
Rodriguez, J.G.; Canoira, L. React. Kinet. Catal. Lett. 1989, 38,351.
[93]
Chouhan, M.; Kumar, K.; Sharma, R.; Grover, V.; Nair, V.A. Tetrahedron Lett. 2013, 54,4540.
[94]
Taniguchi, T.; Ogasawara, K. Angew. Chem., nt. Ed. 1998, 37,1136.
[95]
Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39,4679.
[96]
Kim, S.; Jo, J.; Lee, D. Org. Lett. 2016, 18,4530.
[97]
Gaertner, D.; Konnerth, H.; von Wangelin, A.J. Catal. Sci. Technol. 2013, 3,2541.
[98]
Iqbal, J.; Srivastava, R.R. Tetrahedron 1991, 47,3155.
[99]
Giedyk, M.; Turkowska, J.; Lepak, S.; Mar-culewicz, M.; Proinsias, K.O.; Gryko, D. Org. Lett. 2017, 19,2670.
[100]
Hemming, D.S.; Talbot, E.P.; Steel, P.G. Tetrahedron Lett. 2017, 58,17.
[101]
Torii, S.; Tanaka, H.; Katoh, T.; Morisaki, K. Tetrahedron Lett. 1984, 25,3207.
[102]
Espanet, B.; Du?ach, E.; Périchon, J. Tetrahedron Lett. 1992, 33,2485.
[103]
Olivero, S.; Du?ach, E. J. Chem. Soc., hem. Commun. 1995,2497.
[104]
Yasuhara, A.; Kasano, A.; Sakamoto, T. J. Org. Chem. 1999, 64,4211.
Outlines

/