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
收藏
页码：17082 / +
页数：3
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