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...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-12, Vol.59 (49), p.21959-21964
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
hydrogen borrowing
Ruthenium
ruthenium catalyst
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
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:1433-7851
1521-3773
DOI:10.1002/anie.202009754