Dynamic kinetic resolution of beta-azido alcohols. An efficient route to chiral aziridines and beta-amino alcohols

O Pàmies; J E Bäckvall

doi:10.1021/jo015579d

Dynamic kinetic resolution of beta-azido alcohols. An efficient route to chiral aziridines and beta-amino alcohols

J Org Chem. 2001 Jun 1;66(11):4022-5. doi: 10.1021/jo015579d.

Authors

O Pàmies¹, J E Bäckvall

Affiliation

¹ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.

PMID: 11375029
DOI: 10.1021/jo015579d

Abstract

Enzymatic resolution of beta-azido alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic beta-azido alcohols were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and conversion up to 98%). The synthetic utility of this procedure has been illustrated by the practical synthesis of (S)-propanolol I and (R)-beta-azido-alpha-(4-methoxyphenyl)ethanol ((R)-1c), a direct precursor of denopamine II.