Catalytic asymmetric synthesis of 3-hydroxyl-2-oxindoles via enantioselective Morita-Baylis-Hillman reaction of isatins

被引：43
|
作者：
Wang, Ci-Ci
Wu, Xin-Yan [1 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 16期
基金：
中国国家自然科学基金;
关键词：
Enantioselective organocatalysis; Morita-Baylis-Hillman reaction; Bifunctional phosphinothiourea; Isatin; 3-Hydroxyl-2-oxindole; ARYLBORONIC ACIDS; ADDUCTS; DERIVATIVES; PHOSPHINOTHIOUREA; OXINDOLES; ALDEHYDES; (R)-CONVOLUTAMYDINE; CONSTRUCTION; ALLYLATION; ALKALOIDS;
D O I：
10.1016/j.tet.2011.02.045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective Morita-Baylis-Hillman reaction of acrylates to isatins was investigated for the first time, employing bifunctional phosphinothiourea organocatalysts based on chiral cyclohexane scaffold. The 3-hydroxyl-2-oxindole derivatives were obtained in excellent yields with moderate enantioselectivity (up to 69% ee) in the presence of 10 mol % catalyst 1b. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2974 / 2978
页数：5
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