Asymmetric synthesis of the 4-hydroxymethyl-2-oxazolidinone from the serinol derivative and chloroformates

被引：19

作者：

Sugiyama, S ^{[1
]}

Watanabe, S ^{[1
]}

Ishii, K ^{[1
]}

机构：

[1] Meiji Pharmaceut Univ, Tokyo 2048588, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 42期

关键词：

diastereoselection; oxazolidinones; amino alcohols; cyclization;

D O I：

10.1016/S0040-4039(99)01548-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric desymmetrization of 2-[(alpha R)-alpha-methylbenzyl]amino-1,3-propanediol (1) with 2-chloroethyl chloroformate and DBU at room temperature gave optically active (4S)-4-hydroxymethyl-N-[(alphaR)-alpha-methylbenzyl]-2-oxazolidinone [(4S)-2] (up to 94% de). This reaction involves kinetic resolution and [1,3]-alkoxyacyl migration of 2-chloroethyl (2S)- and 2-chloroethyl (2R)-3-hydroxy-2-[(alpha R)-alpha-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4]. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7489 / 7492

页数：4

共 16 条

[1]

BANFI L, 1993, SYNTHESIS-STUTTGART, P1029

[2]

Choi SK, 1998, HETEROCYCLES, V48, P1917

[3] Stereoselective synthesis of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via trimethylstannyl-mediated radical carbocyclization and oxidative destannylation [J].