SN1-Type Reactions in the Presence of Water: Indium(III)-Promoted Highly Enantioselective Organocatalytic Propargylation of Aldehydes

被引：68

作者：

Sinisi, Riccardo ^{[1
]}

Vita, Maria Victoria ^{[1
]}

Gualandi, Andrea ^{[1
]}

Emer, Enrico ^{[1
]}

Cozzi, Pier Giorgio ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 27期

关键词：

aldehydes; enamine; indium; organocatalysis; propargylation; ASYMMETRIC ALKYLATION; ALPHA-ALKYLATION; CATALYSIS; ADVENT; GOLD;

D O I：

10.1002/chem.201100729

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Water under troubled chemistry! The first catalytic stereoselective addition of aldehydes to internal functionalized propargylic alcohols promoted by a combination of organocatalysis and indium triflate is described (see scheme). The reaction is tolerant of functional groups (FG) and was performed in the presence of water. High enantioselectivities (anti, 92-99 % ee) and moderate diastereomeric ratios (d.r., up to 6.7:1 for the anti isomer) were obtained. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7404 / 7408

页数：5

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