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The stereospecific synthesis of all four stereoisomers of 2-amino-6-phenoxy-cyclohexanol,

✍ Scribed by Edouard Lier; Richard Berthold; Franz Troxler

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
534 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Epoxidation of 3‐phenoxycyclohexene 5 with m‐chloro‐perbenzoic acid gave 6 and 7 in a ratio of 9:1. These two epoxides were heated with a series of amines to give the aminophenoxycyclohexanol derivatives 1 and 2 respectively; in all cases the reaction was regio‐ and stereospecific. Two methods based on the principle of neighbouring group participation were developed to synthesize the cis‐amino alcohols 3 and 4. In the first, the hydroxy group was used to introduce an amine function at the vicinal carbon atom. In the second method, the amino group served as the point of reference and the configuration of the adjacent alcohol function was inverted.

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