ol048322l_si_001.pdf (1.79 MB)
Asymmetric Catalytic Synthesis of Enantiopure N-Protected 1,2-Amino Alcohols
journal contributionposted on 2004-10-28, 00:00 authored by Giuseppe Bartoli, Marcella Bosco, Armando Carlone, Manuela Locatelli, Paolo Melchiorre, Letizia Sambri
The asymmetric aminolytic kinetic resolution (AKR) of racemic terminal epoxides using carbamates as the nucleophile catalyzed by (salen)CoIII 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.