E. Lier, R. Berthold, F. Troxler
Jun 8, 1979
Citations
0
Influential Citations
4
Citations
Journal
Helvetica Chimica Acta
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.