超越氮杂-Morita-Baylis-Hillman 反应：N-Boc-亚胺与乙基 2,3-丁二烯酸酯的路易斯碱催化反应。

Beyond the aza-Morita-Baylis-Hillman reaction: Lewis base-catalyzed reactions of N-Boc-imines with ethyl 2,3-butadienoate.

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.

出版信息

J Org Chem. 2009 Aug 21;74(16):6343-6. doi: 10.1021/jo9008832.

DOI:10.1021/jo9008832

PMID:19624114

Abstract

Lewis base catalyzed reactions of N-Boc-imines and ethyl 2,3-butadienoate were investigated systematically. The normal aza-Morita-Bylis-Hillman products were obtained in good to excellent yields catalyzed by DABCO. When PPh(3) was used as the catalyst, novel rearrangement product (E)-ethyl 2-((Z)-(tert-butoxycarbonylimino)(aryl)methyl)but-2-enoates could be formed in moderate yields.

摘要

系统研究了 N-Boc-亚胺和乙基 2,3-丁二烯酸乙酯的路易斯碱催化反应。在 DABCO 的催化下，得到了正常的氮杂-Morita-Bylis-Hillman 产物，产率良好到优秀。当使用 PPh(3)作为催化剂时，可中等产率得到新型重排产物(E)-乙基 2-((Z)-(叔丁氧羰基亚氨基)(芳基)甲基)丁-2-烯酸乙酯。