不对称有机催化的 3-甲基-5-芳基呋喃-2(3H)-酮与 N-(2-吡啶磺酰基)亚胺的烯醇式 Mannich 反应：δ-氨基 γ,γ-二取代丁烯内酯的对映选择性合成。
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.
机构信息
Institute for Advanced Study, Chengdu University, Chengdu 610106, China.
出版信息
Org Biomol Chem. 2018 Mar 7;16(10):1636-1640. doi: 10.1039/c7ob03117c.
PMID:29451583
Abstract
An asymmetric organocatalytic vinylogous Mannich reaction of 3-methyl-5-arylfuran-2(3H)-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).
摘要
一种不对称的有机催化乙烯基曼尼希反应，涉及 3-甲基-5-芳基呋喃-2(3H)-酮与 N-(2-吡啶磺酰)亚胺的反应，已在 5 mol%硫脲-叔胺作为催化剂的条件下得到发展。一系列含有相邻季碳和叔碳立体中心的 δ-氨基 γ,γ-二取代丁烯内酯以令人满意的结果（高达 90%的产率、90:10 dr 和 95:5 er）得到有效制备。
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