Asymmetric synthesis of pyrano[2,3-c]pyrazoles via a cascade reaction between Morita-Baylis-Hillman acetates of nitroalkenes and pyrazolones

被引：30
|
作者：
Xie, Jin
Sha, Feng
Wu, Xin-Yan [1 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
来源：
TETRAHEDRON | 2016年 / 72卷 / 27-28期
基金：
中国国家自然科学基金;
关键词：
Cascade reaction; Enantioselective organocatalysis; MBH acetates; Pyrano[2,3-c]pyrazoles; Squaramide; ENANTIOSELECTIVE SYNTHESIS; NITROALLYLIC ACETATES; MICHAEL ADDITION; CONSTRUCTION; SQUARAMIDES; ORGANOCATALYSTS; CYCLOADDITIONS; DERIVATIVES; ACTIVATION; DESIGN;
D O I：
10.1016/j.tet.2016.05.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first organocatalytic enantioselective cascade reaction of Morita-Baylis-Hillman acetates of nitroalkenes with pyrazolones has been developed. With 20 mol % of chiral tertiary-amine squaramide, 1,4,5,6-tetrahydropyrano[2,3-c]pyrazoles were afforded in moderate yields (up to 71%) with excellent stereoselectivities (up to>99:1 dr and up to 98% ee). (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4047 / 4054
页数：8
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