A new chiral oxazoline derived from camphor and its conversion to (R)-2-methylalkanoic acids

被引：6

作者：

Chandrasekhar, S ^{[1
]}

Kausar, A ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)00197-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(1S,5R,7R)-(-)-10, 10-Dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.0(1,5)]dec-2-ene 2 was prepared in 95% yield from (1S)-1-amino-2-exo-hydroxyapocamphane 1. The chiral oxazoline could be alkylated (LDA/THF/-78 degrees C/RX, RX = ethyl, n-propyl, n-butyl iodides or benzyl bromide) to 3 in 95% yield and > 95% diastereoselectivity, and the products hydrolysed to (R)-2-methylalkanoic acids 4 (43-47% yield, 93-98% e.e.). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2249 / 2253

页数：5

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