Enantioselective synthesis of chiral α, β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α, β-unsaturated γ-butyrolactam to 2-enoylpyridines. Issue 27 (15th June 2016)

• Record Type: Journal Article
• Authors: Wang, Zhen-Hua; Wu, Zhi-Jun; Yue, Deng-Feng; You, Yong; Xu, Xiao-Ying; Zhang, Xiao-Mei; Yuan, Wei-Cheng
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 27(2016)
• Page Start: 6568
• Page End: 6576
• Publication Date: 2016-06-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01191h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Approach providing a series of optically active α, β-unsaturated γ-substituted butyrolactams in high yields with excellent diastereo- and enantioselectivities. Abstract : An organocatalyzed direct asymmetric vinylogous Michael addition reaction of α, β-unsaturated γ-butyrolactam to 2-enoylpyridines has been developed with a chiral bifunctional amine-squaramide as the catalyst. This approach provides easy access to a series of optically active α, β-unsaturated γ-substituted butyrolactams in high yields (up to 99%) with excellent diastereoselectivities (up to >99 : 1) and enantioselectivities (up to >99% ee).