Chiral‐Organotin‐Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5‐trifluorophenyl groups at the 3,3′‐positions of the binaphthyl framework enabled this transformation with excellent yield and high e...

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Published in:Angewandte Chemie International Edition 2019-11, Vol.58 (45), p.16177-16180
Main Authors: Yang, Hui, Zheng, Wen‐Hua
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
amino alcohols
Aromatic compounds
Catalysts
chiral resolution
Enantiomers
kinetic resolution
Organotin
organotin complexes
Organotin compounds
Substrates
Tin
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description A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5‐trifluorophenyl groups at the 3,3′‐positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl‐ and alkyl‐substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500. A valuable structural motif in many biologically active compounds, the vicinal amino alcohol unit can be obtained in optically active form by kinetic resolution of the racemate. A chiral organotin complex catalyzes this reaction, which is thought to proceed via a stannylene N,O‐aminal intermediate.
doi_str_mv 10.1002/anie.201909700
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subjects Alcohol
Alcohols
amino alcohols
Aromatic compounds
Catalysts
chiral resolution
Enantiomers
kinetic resolution
Organotin
organotin complexes
Organotin compounds
Substrates
Tin
title Chiral‐Organotin‐Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
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