Platinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperature

被引：13

作者：

Kiyooka, Syun-ichi ^{[1
]}

Matsumoto, Satoshi ^{[1
]}

Shibata, Tomonori ^{[1
]}

Shinozaki, Kei-ichi ^{[1
]}

机构：

[1] Kochi Univ, Dept Mat Sci, Fac Sci, Kochi 7808520, Japan

来源：

TETRAHEDRON | 2010年 / 66卷 / 10期

基金：

日本学术振兴会;

关键词：

{(R)-Binap}Pt(mu-OH)](22)SbF6; Platinum-catalyzed enantioselective aldol reaction; Mukaiyama aldol reaction; BAEYER-VILLIGER OXIDATION; PALLADIUM(II) COMPLEXES; HYDROXO COMPLEXES; ALDEHYDES; ENOLATE; CONDENSATION; PEROXIDE; KETONES; WATER;

D O I：

10.1016/j.tet.2010.01.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[{(R)-binap}Pt(mu-OH)](2)2X is a weak Lewis acid, which can catalyze the enantioselective aldol reaction of aldehydes with ketene silyl acetals in DMF at room temperature. The platinum(II) complex-catalyzed the enantioselective aldol reaction of aldehydes with 1-methoxy-2-methyl-(1-trimethylsilyloxy)propene gave the corresponding aldols in high yields with enantioselectivity up to 92%. With 5 mol % loading of the complexes, the enantioselective aldol reaction of aldehydes with 1-benzyloxy-1-(trimethylsilyloxy)propene smoothly proceeded in DMF containing 10% HMPA as to predominantly give anti-propionates with enantioselectivity up to 89%, irrespective of the silyl nucleophile geometry. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1806 / 1816

页数：11

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