Enantioselective synthesis of (2-pyridyl)alanines via catalytic hydrogenation and application to the synthesis of L-azatyrosine

被引：25

作者：

Adamczyk, M ^{[1
]}

Akireddy, SR ^{[1
]}

Reddy, RE ^{[1
]}

机构：

[1] Abbott Labs, Div Diagnost, Dept Chem 9 NM, Abbott Pk, IL 60064 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol016455q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS A novel method for the synthesis of (2-pyridyl)alanines 2a-b was developed by converting (2-pyridyl)dehydroamino acid derivatives 1a-b to the corresponding N-oxides 3a-b followed by asymmetric hydrogenation using (RR)-[Rh(Et-DUPHOS)(COD)]BF4 [(RR)-6] catalyst and subsequent N-oxide reduction in 80-83% ee. This methodology was applied to the total synthesis of L-azatyrosine [(+)-12], an antitumor antibiotic, starting from (5-benzyloxy)-2-pyridylmethanol (7), in > 96% enantiomeric purity.

引用

页码：3157 / 3159

页数：3

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