Diastereoselective Mukaiyama aldol reaction of (N-alkyl) isatins with 2-(trimethylsilyloxy)furan by using lanthanum triflate

被引：22

作者：

Meshram, Harshadas Mitaram ^{[1
]}

Ramesh, Palakuri ^{[1
]}

Reddy, Bandi Chennakesava ^{[1
]}

Sridhar, Balasubramanian ^{[2
]}

Yadav, Jhillu Singh ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2011年 / 67卷 / 17期

关键词：

Mukaiyama aldol reaction; Isatins; 2-(trimethylsilyloxy)furan; La(OTf)(3); ENANTIOSELECTIVE TOTAL-SYNTHESIS; CATALYZED ASYMMETRIC ADDITION; SUBSTITUTED ISATINS; ARYLBORONIC ACIDS; ALDEHYDES; DERIVATIVES; ALPHA; 2-TRIMETHYLSILYLOXYFURAN; CONDENSATION; OXINDOLES;

D O I：

10.1016/j.tet.2011.02.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient vinylogous Mukaiyama aldol reaction (VMAR) of 2-(trimethylsilyloxy)furan with various (N-alkyl)isatins is described in the presence of lanthanum(III) triflates (5 mol %). The reaction proceeds rapidly and affords the corresponding 3-hydroxy-(5-oxo-2,5-dihydrofuran-2-yl)indolin-2-one in high yields with good diastereoselectivities (threo:erythro ratio up to <= 95:5). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3150 / 3155

页数：6

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