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The stereospecific synthesis of all four stereoisomers of 2‐amino‐6‐phenoxy‐cyclohexanol ,
Author(s) -
Lier Edouard,
Berthold Richard,
Troxler Franz
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620403
Subject(s) - chemistry , stereospecificity , cyclohexanol , vicinal , amine gas treating , carbon atom , asymmetric carbon , stereochemistry , alcohol , group (periodic table) , walden inversion , medicinal chemistry , organic chemistry , optically active , catalysis , ring (chemistry)
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.