Tetrahedron letters

Stereocontrol in the reduction of 1, 2-diimine with an oxazaborolidine catalyst. Highly stereoselective preparation of (R, R)-1, 2-diphenylethylenediamine

M Shimizu, M Kamei, T Fujisawa

Index: Shimizu, Makoto; Kamei, Mie; Fujisawa, Tamotsu Tetrahedron Letters, 1995 , vol. 36, # 47 p. 8607 - 8610

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Citation Number: 61

Abstract

Highly enantioselective reduction of 1, 2-bis (p-methoxyphenylimino)-1, 2-diphenylethane was conducted even with 0.5 mol% of new oxazaborolidine derived form L-threonine and a stoichiometric amount of BH3· THF to give 1, 2-diphenylethylenediamine derivative in excellent enantiomeric purity. The subsequent deprotection of nitrogen atoms afforded (R, R)-1, 2-diphenylethylenediamine in enantiomerically pure form.