Abstract
Reaction of (E)-(S)-N-(1-isopropyl-2-methoxyethyl)benzylideneamine (2) with ethylmagnesium bromide gave a mixture of (1S, 1'S)- and (1R, 1'S)-N-(1'-isopropyl-2'-methoxyethyl)-1-phenylpropylamines (3) (91 : 9%). (E)-(S)-N-(1-Isopropyl-2-methoxyethyl)propylideneamine (5) was treated with phenyllithium to give (1R, 1'S)- and (1S, 1'S)-3 (95 : 5%). On the other hand, reaction of (E)-(S)-N-(2-hydroxy-1-isopropylethyl)benzylideneamine (6) with ethylmagnesium bromide yielded a mixture of (1S, 1'S)- and (1R, 1'S)-N-(2'-hydroxy-1'-isopropylethyl)-1-phenylpropylamines (7) (78 : 22%). The absolute configurations of these amines were determined by circular dichroism (CD) spectroscopy and comparison with authentic samples synthesized by alternative methods.
