Construction of Contiguous Tetrasubstituted Chiral Carbon Stereocenters via Direct Catalytic Asymmetric Aldol Reaction of α-Isothlocyanato Esters with Ketones

被引：115

作者：

Yoshino, Tatsuhiko ^{[1
]}

Morimoto, Hiroyuki ^{[1
]}

Lu, Gang ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 47期

关键词：

ENANTIOSELECTIVE SYNTHESIS; AMINO-ACIDS; TERTIARY ALCOHOLS; ALDEHYDES; CONDENSATION; DERIVATIVES; KETIMINES; ADDITIONS;

D O I：

10.1021/ja908571w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol. reaction of a-substituted a-isothiocyanato esters with unactivated simple ketones is described. A Bu2Mg/Schiff base catalyst promoted the aldol addition/cyclization sequence at room temperature, giving protected alpha-amino-beta-hydroxy esters with contiguous tetrasubstituted chiral carbon stereocenters in 99 to 68% yield, 98:2 to 74:26 dr, and 98 to 82% ee.

引用

页码：17082 / +

页数：3

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