Synthesis of a biphenyl-based axially chiral amino acid as a highly efficient catalyst for the direct asymmetric aldol reaction

被引：60
|
作者：
Kano, Taichi [1 ]
Tokuda, Osamu [1 ]
Maruoka, Keiji [1 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 42期
关键词：
aldol reaction; amino acid; organocatalysis;
D O I：
10.1016/j.tetlet.2006.08.051
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A biphenyl-based axially chiral amino acid (S)-2 has been designed and synthesized. The new amino acid (S)-2 has been found to be a more efficient catalyst than (S)-1 in the direct asymmetric aldol reaction of acetone with aldehydes. For instance, the use of only 0.1 mol % of (S)-2 was sufficient to complete the reaction between acetone and 4-nitrobenzaldehyde, giving the corresponding aldol adduct in good yield with an excellent enantioselectivity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7423 / 7426
页数：4
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