Base-catalyzed reaction between isatins and N-Boc-3-pyrrolin-2-one

被引：19
|
作者：
Ramireddy, Naresh [1 ]
Zhao, John C. -G. [1 ]
机构：
[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 03期
关键词：
Isatin; 3-Pyrrolin-2-one; Catalysis; Mechanism; Morita-Baylis-Hillman reaction; ASYMMETRIC ALDOL REACTION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; BAYLIS-HILLMAN REACTION; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED KETONES; 3-HYDROXY OXINDOLES; VINYLOGOUS ALDOL; ORGANOCATALYSTS; (R)-CONVOLUTAMYDINE; CONSTRUCTION;
D O I：
10.1016/j.tetlet.2013.11.118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The base-catalyzed reaction between isatins and N-Boc-3-pyrrolin-2-one yields Morita-Baylis-Hillman (MBH) adducts instead of the expected aldol products in good to high yields (up to 97%). Various organic and inorganic bases are efficient catalysts for this reaction. Our study excluded the Morita-Baylis-Hillman mechanism for the formation of the MBH-type products. The MBH products are most likely formed as a result of the subsequent isomerization of the original aldol products between isatins and N-Boc-3-pyrrolin-2-one. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：706 / 709
页数：4
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