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Asymmetric Vinylogous Mannich Reactions: A Versatile Approach to Functionalized Heterocycles

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Asymmetric Vinylogous Mannich Reactions A Versatile Approach to Functionalized Heterocycles.htm (392bytes)
Date
2011-07-19
Author
Ruan, Shu-Tang
Luo, Jie-Min
Du, Yu
Huang, Pei-Qiang
黄培强
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  • 化学化工-已发表论文 [14469]
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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.
Citation
Org. Lett., 2011, 13 (18): 4938–4941
URI
http://dx.doi.org/doi:10.1021/ol2020384
https://dspace.xmu.edu.cn/handle/2288/11512
WOS:000294703900048

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