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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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
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cited_by cdi_FETCH-LOGICAL-c3734-32b1e68150d0fb1d896289715c8448164969232b157d423933da8a0859c092063
cites cdi_FETCH-LOGICAL-c3734-32b1e68150d0fb1d896289715c8448164969232b157d423933da8a0859c092063
container_end_page 21964
container_issue 49
container_start_page 21959
container_title Angewandte Chemie International Edition
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creator Xu, Ruirui
Wang, Kun
Liu, Haoying
Tang, Weijun
Sun, Huaming
Xue, Dong
Xiao, Jianliang
Wang, Chao
description 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).
doi_str_mv 10.1002/anie.202009754
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source Wiley-Blackwell Read & Publish Collection
subjects Alcohol
Alcohols
allylic alcohol
Amines
amino alcohol
asymmetric catalysis
Catalysis
hydrogen borrowing
Ruthenium
ruthenium catalyst
Substrates
title Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols
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