Diastereoselective formation of tricarbonyliron(0) complexes of 1-aza-1,3-dienes bearing chiral substituents

Abstract

Syntheses of two series of novel 1-aza-1,3-dienes bearing chiral substituents on nitrogen [PhCHCHCHNCH(R)Ph (R = Et, Prⁱ and Bu^t) and PhCHCHCHNCH(R)Me (R = Et, Prⁱ and Bu^t)] are described and the stereochemical outcome of their complexation reactions with Fe₂(CO)₉ reported. Diastereoisomeric ratios of 93:7 and 94:6 are observed on complexation of PhCHCHCHNCH(Bu^t)Ph 10 and PhCHCHCHNCH(Bu^t)Me 19 respectively. The structures of the major diastereoisomers of 10 and 19 have been determined by NOE measurements.