Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols

A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantio...

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Bibliographic Details
Published in:Angewandte Chemie 2020-12, Vol.132 (49), p.22143-22148
Main Authors: Xu, Ruirui, Wang, Kun, Liu, Haoying, Tang, Weijun, Sun, Huaming, Xue, Dong, Xiao, Jianliang, Wang, Chao
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
allylic alcohol
Amines
amino alcohol
asymmetric catalysis
Catalysis
Chemistry
hydrogen borrowing
Ruthenium
ruthenium catalyst
Substrates
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Summary:A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantiomerically enriched chiral γ‐amino alcohols with broad substrate scope and excellent enantioselectivities (68 examples, up to >99 % ee). Anti‐Markovnikov hydroamination of racemic allylic alcohols produces chiral γ‐amino alcohols, which are key intermediates for the synthesis of many drugs and biologically active molecules. Driven by a ruthenium catalyst via a hydrogen borrowing pathway, the reaction features a broad substrate scope (68 examples) and excellent enantioselectivities (up to >99 % ee).
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202009754