Stereoselective synthesis of 4-hydroxy-2-phenylproline framework

被引：21

作者：

Maeda, K

Miller, RA

Szumigala, RH

Shafiee, A

Karady, S

Armstrong, JD

机构：

[1] Banyu Pharmaceut Co Ltd, Proc Res, Okazaki, Aichi 4440858, Japan

[2] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 09期

关键词：

4-hydroxyproline; optical resolution; phase transfer reaction; iodo cyclization; halo lactonization;

D O I：

10.1016/j.tetlet.2004.12.130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.

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页码：1545 / 1549

页数：5

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