Remarkable Diastereoselectivity in the Addition of Allylic and Unsaturated Diorganozinc Reagents to β-(<i>N</i>,<i>N</i>-Dialkylamino)-aldehydes

Abstract

1,3-Anti amino alcohols 5(a)-18(a) are obtained with high diastereoselectivity by use of diorganozinc reagents in additions to amino aldehydes 2a and 2b. The corresponding Grignard reagents exhibit low to modest diastereoselectivity. The highly diastereoselective zinc-based method makes available a wide range of 4,4-disubstituted cyclohexenone derivatives containing contiguous stereocenters.