A highly efficient asymmetric synthesis of methoxyhomophenylalanine using Michael addition of phenethylamine.

被引：49

作者：

Yamada, M ^{[1
]}

Nagashima, N ^{[1
]}

Hasegawa, J ^{[1
]}

Takahashi, S ^{[1
]}

机构：

[1] Kaneka Corp, Fine Chem Div, Fine Chem Res Labs, Takasago, Hyogo 676, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(98)02023-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method for (S)-p-methoxyhomophenylalanine (S)-1 by using diastereoselective Michael addition as a key step was reported. Thus, the Michael addition of(S)1-phenethylamine (S)-3 to p-methoxy-trans-benzoylacrylic acid 2 was performed in a highly stereoselective (up to 98% d.e. and up to 90% yield) fashion and, subsequently, the resultant adduct 4a was catalytically hydrogenated to afford (S)-1 almost quantitatively. The most likely mechanism of the addition reaction was dynamic resolution. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9019 / 9022

页数：4

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