The stereochemical assignment of the 1,2-Diphenylbut-3-en-1-ols, (1RS,2RS,3RS)- and (1RS,2RS,3SR)-3,4-Epoxy-1,2-diphenylbutan-1-ols and (2RS,3SR)- and (2RS,3RS)-3,4-Epoxy-1,2-diphenylbutan-1-ones and crystal structure of (1RS,2RS,3RS)-3,4-Epoxy-1,2-diphenylbutan-1-ol

Abstract

The reaction of the Grignard compound formed from (E)-3-chloro-1-phenylprop-1-ene (2a) with benzaldehyde has been studied and conditions found which allow for the efficient preparation of the diastereoisomeric homoallylic alcohols (4) and (5). The relative stereochemistry of these alcohols along with (1RS,2RS,3RS)- and (1RS,2RS,3SR)-3,4-epoxy-1,2-diphenylbutan-1-ol (6) and (7) and (2RS,3SR)- and (2RS,3RS)-3,4-epoxy-1,2-diphenylbutan-1-ones (8) and (10) has been established and the crystal structure of (1RS,2RS,3RS)-3,4-epoxy-1,2-diphenylbutan-1-ol determined.