A simple and convenient synthesis of β-amino alcohol chiral auxiliaries based on limonene oxide

Abstract

A series of chiral β-amino alcohols was prepared by the reaction of secondary amines with a 1:1 mixture of cis- and trans-limonene oxide in the presence of water as a catalyst. The β-amino alcohol obtained was derived from the trans-limonene oxide, and the unreacted cis-limonene oxide was recovered from the reaction mixture. The β-amino alcohols are useful chiral auxiliaries for the addition of diethylzinc to benzaldehyde.