SYNTHESIS OF (2S,3R)-3-AMINO-2-HYDROXY-5-METHYLHEXANOIC ACID - BRIDGING EFFECT OF KF

被引：18

作者：

SOLLADIECAVALLO, A

KHIAR, N

机构：

[1] Laboratoire de stereochimie organometallique, EHICS, 67008 Strasbourg, 1, rue Blaise Pascal

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 15期

关键词：

D O I：

10.1021/jo00302a050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Natural (2S,3#)-3-amino-2-hydroxy-5-methylhexanoic acid is synthesized in 53-55% yield (referred to (-)-8-phenylmenthol used as chiral auxiliary) by condensation of l-nitro-3-methylbutane on (-)-8-phenylmenthol glyoxylate hydrate using KF as a mild base. With a large excess of KF in THF it has been possible to increase the diastereoselectivity of the nitro aldol condensation (up to I/II/III/IV = 77/13/10/0). © 1990, American Chemical Society. All rights reserved.

引用

页码：4750 / 4754

页数：5

共 27 条

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[2]

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