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American Chemical Society, Organic Letters, 18(13), p. 4938-4941, 2011

DOI: 10.1021/ol2020384

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Asymmetric Vinylogous Mannich Reactions: A Versatile Approach to Functionalized Heterocycles

Journal article published in 2011 by Shu-Tang Ruan, 黄培强, Jie-Min Luo, Yu Du, Pei-Qiang Huang ORCID
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

Asymmetric vinylogous Mannich reaction (VMR) of 2-(tert-butyldimethylsilyloxy)furan (TBSOF, 1) with (R(S))- or (S(S))-t-BS-imines (3) furnished 5-aminoalkylbutenolides 7a-k in 75-87% yields with anti/syn ratios ranging from 75:25 to 97:3. Butenolides 7a-f,k were readily converted into substituted lactones 8 and 5 and 6-substituted 5-hydroxypiperidin-2-ones 11a-g, which are, in turn, key intermediates for the synthesis of many bioactive compounds. ; National Basic Research Program (973 Program) of China[2010CB833200]; NSF of China[20832005, 21072160]