An asymmetric organocatalytic vinylogous Mannich reaction of 3-methyl-5-arylfuran-2(3H)-ones with N-(2-pyridinesulfonyl) imines: enantioselective synthesis of δ-amino γ, γ-disubstituted butenolides. Issue 10 (16th February 2018)

• Record Type: Journal Article
• Authors: Wang, Zhen-Hua; You, Yong; Chen, Yong-Zheng; Xu, Xiao-Ying; Yuan, Wei-Cheng
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 10(2018)
• Page Start: 1636
• Page End: 1640
• Publication Date: 2018-02-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob03117c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A series of δ-amino γ, γ-disubstituted butenolides were obtained with satisfactory results via an asymmetric vinylogous Mannich reaction of 3-methyl-5-arylfuran-2(3 H )-ones with N -(2-pyridinesulfonyl)imines. Abstract : An asymmetric organocatalytic vinylogous Mannich reaction of 3-methyl-5-arylfuran-2(3 H )-ones with N -(2-pyridinesulfonyl)imines has been developed with 5 mol% thiourea–tertiary amine as the catalyst. A series of δ-amino γ, γ-disubstituted butenolides bearing adjacent quaternary and tertiary stereocenters are efficiently obtained with satisfactory results (up to 90% yield, 90 : 10 dr, and 95 : 5 er).