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

页码：706 / 709

页数：4

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