Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols

Giuseppe Bartoli; Marcella Bosco; Armando Carlone; Manuela Locatelli; Paolo Melchiorre; Letizia Sambri

doi:10.1021/ol048322l

Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols

Org Lett. 2004 Oct 28;6(22):3973-5. doi: 10.1021/ol048322l.

Authors

Giuseppe Bartoli¹, Marcella Bosco, Armando Carlone, Manuela Locatelli, Paolo Melchiorre, Letizia Sambri

Affiliation

¹ Department of Organic Chemistry A. Mangini, University of Bologna v.le Risorgimento 4, 40136 Bologna, Italy. giuseppe.bartoli@unibo.it

PMID: 15496077
DOI: 10.1021/ol048322l

Abstract

[reaction: see text] The asymmetric aminolytic kinetic resolution (AKR) of racemic terminal epoxides using carbamates as the nucleophile catalyzed by (salen)Co(III) complex provides a practical and straightforward method for the synthesis of both aliphatic and aromatic N-Boc- or N-Cbz-protected 1,2-amino alcohols in almost enantiomerically pure form (ee >/= 99%). The AKR uses an easily accessible catalyst and inexpensive starting materials, and the reactions are conveniently carried out at room temperature under an air atmosphere.