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Asymmetric Vinylogous Mannich Reactions: A Versatile Approach to Functionalized Heterocycles

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journal contribution
posted on 16.09.2011, 00:00 by Shu-Tang Ruan, Jie-Min Luo, Yu Du, Pei-Qiang Huang
Asymmetric vinylogous Mannich reaction (VMR) of 2-(tert-butyldimethylsilyloxy)furan (TBSOF, 1) with (RS)- or (SS)-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.