Catalytic, enantioselective alkylations of N,O- and N,N-acetals and hemiacetals

被引：41
|
作者：
Ferraris, D [1 ]
Young, B [1 ]
Dudding, T [1 ]
Drury, WJ [1 ]
Lectka, T [1 ]
机构：
[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 29期
关键词：
asymmetric synthesis; amino acids; acetals; copper;
D O I：
10.1016/S0040-4020(99)00450-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the first examples of catalytic, enantioselective alkylation of N,O-acetals to produce useful amino acid derivatives 5 in high yield (73-93%) and enantioselectivity (70-96%). We have extended the utility of our reaction to include a simple one-pot procedure from readily available starting materials. We also provide several different N-based protecting groups that greatly increase the flexibility of the reaction. In addition, we have elucidated novel mechanistic information including the discovery of unique transilylations that start off the catalytic reactions of enol silane nucleophiles with N,O-acetals. These details will guide us in further explorations of the reaction's scope and utility. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8869 / 8882
页数：14
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