☆ 4.8 Article

Hybrid Organo- and Biocatalytic Process for the Asymmetric Transformation of Alcohols into Amines in Aqueous Medium

ACS CATALYSIS (2017)

Journal

ACS CATALYSIS

Volume 7, Issue 7, Pages 4768-4774

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acscatal.7b01543

Keywords

one-pot reaction; organocatalysis; biocatalysis; asymmetric synthesis; amino alcohols; transaminase; AZADO

Categories

Chemistry, Physical

Funding

European Union's Horizon 2020 MSCA ITN-EID program [634200]
MINECO under Torres-Quevedo program [PTQ-12-05 407]
Principado de Asturias [FC-15-GRUPIN-14-002]

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Abstract

A hybrid organo- and biocatalytic system for the asymmetric conversion of racemic alcohols into amines was developed. Combining an organocatalyst, AZADO, an oxidant, NaOCl, and an enzyme, omega-transaminase, we implemented a one-pot oxidation-transamination sequential process in aqueous medium. The method showed broad substrate scope and was successfully applied to conventional secondary alcohols and sterically hindered beta-substituted cycloalkanols, where a highly stereoselective dynamic asymmetric bioamination enabled us to set up both contiguous stereocenters with very high enantio- and diastereomeric ratio (>90% yield, >99% ee, and up to 49:1 dr).

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