Samarium Diiodide Promoted the Addition-Ring-Opening Reaction of 2-Piperidinone with α,β-Unsaturated Esters

doi:10.6023/cjoc202106040

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4320-4326.DOI: 10.6023/cjoc202106040 Previous Articles Next Articles

ARTICLES

二碘化钐促进的2-哌啶酮与α,β-不饱和酸酯的加成-开环反应研究

孙建婷^a^,^b, 陈玲艳^a^,^*(), 魏邦国^b

a 上海工程技术大学化学化工学院上海 201620
b 复旦大学药学院上海 201203

收稿日期:2021-06-22 修回日期:2021-07-20 发布日期:2021-08-24
通讯作者: 陈玲艳
基金资助:
研究生创新(20KY0431)

Samarium Diiodide Promoted the Addition-Ring-Opening Reaction of 2-Piperidinone with α,β-Unsaturated Esters

Jian-Ting Sun^a^,^b, Ling-Yan Chen^a(), Bang-Guo Wei^b

a College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
b School of Pharmacy, Fudan University, Shanghai 201203

Received:2021-06-22 Revised:2021-07-20 Published:2021-08-24
Contact: Ling-Yan Chen
Supported by:
Postgraduate Students Innovation Program(20KY0431)

1. .pdf(1381KB)

Abstract

A convenient approach to N-Boc amino ketones 3a~3l has been developed, which features a SmI₂ prompted one-pot radical addition-ring opening process of 2-piperidinone with α,β-unsaturated esters. Moreover, the indolizidine skeleton (6) has been successfully synthesized from the key methyl (S)-8-((tert-butoxycarbonyl)amino)-5-((tert-butyl- dimethylsilyl)oxy)-4-oxooctanoate (3e), which undergoes one-pot deprotection-condensation-reduction-amination process.

Key words: samarium diiodide, 2-piperidinone, radical addition-ring opening, indolizidine

Cite this article

Jian-Ting Sun, Ling-Yan Chen, Bang-Guo Wei. Samarium Diiodide Promoted the Addition-Ring-Opening Reaction of 2-Piperidinone with α,β-Unsaturated Esters[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4320-4326.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

Figure 1. Several natural molecules containing hydroxyindolizidine skeleton

Entry	Additive (equiv.)	Temp./℃	Time/h	Yield^b/%
1	—	–78~–50	2	31
2	H₂O (4)	–78~–50	2	12
3	H₂O (100)	r.t.	0.5	23
4	MeOH (4)	–78~–50	2	Trace
5	^tBuOH (4)	–78~–50	2	68
6	^tBuOH (4)	–78	2	40

Table 1. Optimization of reaction conditions

Scheme 1. Synthetic route of 2-piperidinone 1b~1e

Table 2. Reaction substrate expansion

Scheme 2. Synthesis of hydroxyindolizidine Reagents and conditions: (a) (1) TFA, DCM, 0 ℃, 8 h; (2) Pd/C, H2, TEA, 48 h. two steps 68%. (b) LDA, PhSeBr, THF, –78 ℃, 65%.(c) H2O2, r.t., 1 h, 64%. (d) LiAlH4, AlCl3, THF, –78 ℃, 2 h, 79%.(e) NaIO4 or H2O2, r.t., 1 h

Figure 2. Crystal structure of compound (S)-5

References 18

[1]	(a) Takahata, H.; Momose, T. The Alkaloids: Chemistry and Pharmacology, Elsevier, Toyama, 1993, pp. 189-256. pmid: 17268613
	(b) Michael, J. P. Nat. Prod. Rep. 2007, 24, 191. pmid: 17268613
[2]	Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645.
[3]	Zhang, J.; Morris-Natschke, S. L.; Ma, D.; Shang, X. F.; Yang, C. J.; Liu, Y. Q.; Lee, K. H. Med. Res. Rev. 2021, 41, 928. doi: 10.1002/med.v41.2
[4]	(a) Guengerich, F. P.; Dimari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. doi: 10.1021/ja00787a080 pmid: 3928564
	(b) Kino, T.; Inamura, N.; Nakahara, K.; Kiyoto, S.; Goto, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 38, 936. pmid: 3928564
	(c) Yu, X.; Zhao, Y.; Wang, L.; Chen, X.; Su, Z.; Zhang, H.; Yuan, Q.; Wang, S. Biomed. Pharmacother. 2016, 84, 1654. doi: 10.1016/j.biopha.2016.10.085 pmid: 3928564
[5]	(a) Hohenschutz, L. D.; ArthurBell, E.; Jewess, P. J.; Leworthy, D. P.; Pryce, R. J.; Arnold, E.; Clardy, J. Phytochemistry 1981, 20, 811. doi: 10.1016/0031-9422(81)85181-3
	(b) Nash, R. J.; Fellows, L. E.; Dring, J. V.; Stirton, C. H.; Carter, D.; Hegarty, M. P.; Bell, E. A. Phytochemistry 1988, 27, 1403. doi: 10.1016/0031-9422(88)80203-6
[6]	Whitby, K.; Pierson, T. C.; Geiss, B.; Lane, K.; Diamond, M. S. J. Virol. 2005, 79, 8698. pmid: 15994763
[7]	Huang, X.; Gao, S.; Fan, L. H.; Yu, S. S.; Liang, X. T. Planta Med. 2004, 70, 441. doi: 10.1055/s-2004-818973
[8]	Dhiman, M.; Parab, R. R.; Manju, S. L.; Desai, D. C.; Mahajan, G. B. Nat. Prod. Commun. 2012, 7, 1171. pmid: 23074899
[9]	Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. doi: 10.1021/ja00528a029
[10]	For the selected SmI₂ activated nitrone: (a) Rehák, J.; Fišera, L.; Kožíšek, J.; Bellovičová, L. Tetrahedron 2011, 67, 5762. doi: 10.1016/j.tet.2011.05.129
	(b) Wu, S.-F.; Zheng, X.; Ruan, Y. P.; Huang, P. Q. Org. Biomol. Chem. 2009, 7, 2967. doi: 10.1039/b906224f
	(c) Wu, S. F.; Ruan, Y. P.; Zheng, X.; Huang, P. Q. Tetrahedron 2010, 66, 1653. doi: 10.1016/j.tet.2010.01.011
	(d) Zhang, H. K.; Xu, S. Q.; Zhuang, J. J.; Ye, J. L.; Huang, P. Q. Tetrahedron 2012, 68, 6656. doi: 10.1016/j.tet.2012.06.006
[11]	For the selected SmI₂ activated aza-hemiacetal: (a) Liu, X. K.; Qiu, S.; Xiang, Y. G.; Ruan, Y. P.; Zheng, X.; Huang, P. Q. J. Org. Chem. 2011, 76, 4952. doi: 10.1021/jo200600n pmid: 15704892
	(b) Hu, K. Z.; Ma, J.; Qiu, S.; Zheng, X.; Huang, P. Q. J. Org. Chem. 2013, 78, 1790. doi: 10.1021/jo301277n pmid: 15704892
	(c) Yoda, H.; Ujihara, Y.; Takabe, K. Tetrahedron Lett. 2001, 42, 9225. doi: 10.1016/S0040-4039(01)02030-5 pmid: 15704892
	(d) Yoda, H.; Kohata, N.; Takabe, K. Synth. Commun. 2003, 33, 1087. doi: 10.1081/SCC-120017130 pmid: 15704892
	(e) Zheng, X.; Feng, C. G.; Ye, J. L.; Huang, P. Q. Org. Lett. 2005, 7, 553. pmid: 15704892
[12]	For the selected SmI₂ activated amide: (a) McDonald, C. E.; Galka, A. M.; Green, A. I.; Keane, J. M.; Kowalchick, J. E.; Micklitsch, C. M.; Wisnoski, D. D. Tetrahedron Lett. 2001, 42, 163. doi: 10.1016/S0040-4039(00)01919-5
	(b) Martin, S. F.; Yang, C. P.; Laswell, W. L.; Rueeger, H. Tetrahedron Lett. 1988, 29, 6685. doi: 10.1016/S0040-4039(00)82428-4
	(c) Yu, H.; Gai, T.; Sun, W. L.; Zhang, M. S. Chin. Chem. Lett. 2011, 22, 379. doi: 10.1016/j.cclet.2010.11.013
	(d) Huang, H.-M.; Procter, D. J. Angew. Chem., Int. Ed. 2017, 56, 14262. doi: 10.1002/anie.201708354
[13]	For the selected SmI₂ activated imide (a) Vacas, T.; Álvarez, E.; Chiara, J. L. Org. Lett. 2007, 9, 5445. doi: 10.1021/ol7023357 pmid: 16866500
	(b) Shi, S.; Szostak, M. Org. Lett. 2015, 17, 5144. doi: 10.1021/acs.orglett.5b02732 pmid: 16866500
	(c) Shi, S.; Szostak, M. Molecules 2017, 22, 2018. doi: 10.3390/molecules22112018 pmid: 16866500
	(d) Ha, D. C.; Yun, C. S.; Lee, Y. J. Org. Chem. 2000, 65, 621. pmid: 16866500
	(e) Farcas, S.; Namy, J.-L. Tetrahedron Lett. 2000, 41, 7299. doi: 10.1016/S0040-4039(00)01137-0 pmid: 16866500
	(f) Jensen, C. M.; Lindsay, K. B.; Taaning, R. H.; Karaffa, J.; Hansen, A. M.; Skrydstrup, T. J. Am. Chem. Soc. 2005, 127, 6544. doi: 10.1021/ja050420u pmid: 16866500
	(g) Hansen, A. M.; Lindsay, K. B.; Sudhadevi Antharjanam, P. K.; Karaffa, J.; Daasbjerg, K.; Flowers, R. A.; Skrydstrup, T. J. Am. Chem. Soc. 2006, 128, 9616. pmid: 16866500
[14]	(a) Liu, R.-C.; Wei, J.-H.; Wei, B.-G.; Lin, G.-Q. Tetrahedron: Asymmetry 2008, 19, 2731.
	(b) Wei, B.-G.; Chen, J.; Huang, P.-Q. Tetrahedron 2006, 62, 190. doi: 10.1016/j.tet.2005.09.112
	(c) Nie, X.-D.; Mao, Z.-Y.; Zhou, W.; Si, C.-M.; Wei, B.-G.; Lin, G.-Q. Org. Chem. Front. 2020, 7, 76. doi: 10.1039/C9QO01292C
	(d) Han, X.-L.; Nie, X.-D.; Feng, Y.-M.; Wei, B.-G.; Si, C.-M.; Lin, G. -Q. Chin. Chem. Lett. 2021, doi: 10.1016/j.cclet.2021.05.003. doi: 10.1016/j.cclet.2021.05.003
[15]	(a) Han, P.; Mao, Z.-Y.; Si, C.-M.; Zhou, Z.; Wei, B.-G.; Lin, G.-Q. J. Org. Chem. 2019, 84, 914. doi: 10.1021/acs.joc.8b02795
	(b) Huang, P. Q.; Chen, G.; Zheng, X. J. Heterocycl. Chem. 2007, 44, 499. doi: 10.1002/jhet.v44:2
	(c) Si, C. M.; Huang, W.; Du, Z. T.; Wei, B. G.; Lin, G. Q. Org. Lett. 2014, 16, 4328. doi: 10.1021/ol5020812
[16]	Kwon, H. Y.; Park, C. M.; Lee, S. B.; Youn, J. H.; Kang, S. H. Chem.-Eur. J. 2008, 14, 1023. doi: 10.1002/(ISSN)1521-3765
[17]	Si, C.-M.; Mao, Z.-Y.; Dong, H. Q.; Du, Z. T.; Wei, B.-G.; Lin, G.-Q. J. Org. Chem. 2015, 80, 5824. doi: 10.1021/acs.joc.5b00803
[18]	CCDC 2090177 (5) contains the supplementary crystallographic data for this paper. These data are free of charge from The Cambridge Crystallographic Centre via www.ccdc.cam.ac.uk/datarequest/cif.

二碘化钐促进的2-哌啶酮与α,β-不饱和酸酯的加成-开环反应研究

Samarium Diiodide Promoted the Addition-Ring-Opening Reaction of 2-Piperidinone with α,β-Unsaturated Esters

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 18

Related Articles 8

Recommended Articles

Metrics

Comments

[1]	Chen Liu, Yan Qi, Yongjun Liu. Recent Development of Samarium Diiodide and Other Samarium Reagents in Organic Transformation [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2202-2216.
[2]	Yang Xiaohui, Gu Xuesong, Bin Huaiyu, Xie Jianhua, Zhou Qilin. Asymmetric Synthesis of (-)-Indolizidine167B and (+)-Coniine [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3963-3968.
[3]	GONG Hong-Ju, JIA Xue-Shun, DI Hong-Bin. New Progress of the Application of Samarium Diiodide in Organic Synthesis [J]. Chin. J. Org. Chem., 2010, 30(07): 939-950.
[4]	YU Hui, SUN Wen-Liang, GAO Rui, ZHANG Mei-Shu. A Facile Route to the Synthesis of N-Substituted β,γ-Unsaturated Amides by Ugi/SmI₂ Reduction [J]. Chin. J. Org. Chem., 2010, 30(06): 890-893.
[5]	Nin, Lifei ^a,b Ba, Hang ^a Haji, Akberaisa ^*,a. Progress in Total Synthesis of Swainsonine [J]. Chin. J. Org. Chem., 2009, 29(9): 1354-1361.
[6]	WANG, Kai-Liang; WANG, Qing-Min*; HUANG, Run-Qiu. Synthesis of 14-Hydroxyphenanthro[9,10,3’,4’]indolizidine and Its Biological Activities [J]. Chin. J. Org. Chem., 2008, 28(10): 1826-1829.
[7]	XU Fan, ZHU Xue-Hua, SHEN Qi. Organic Reactions with Samarium Diiodide as a Precatalyst [J]. Chinese Journal of Organic Chemistry, 2004, 24(8): 872-881.
[8]	Zhao Jingrui;Jia Xueshun;Zhai Hongbin. Application of SmI2 in Organic Synthesis [J]. Chin. J. Org. Chem., 2003, 23(6): 499-512.