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

Ruirui Xu; Kun Wang; Haoying Liu; Weijun Tang; Huaming Sun; Dong Xue; Jianliang Xiao; Chao Wang

doi:10.1002/anie.202009754

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

Angew Chem Int Ed Engl. 2020 Dec 1;59(49):21959-21964. doi: 10.1002/anie.202009754. Epub 2020 Sep 30.

Authors

Ruirui Xu¹, Kun Wang¹, Haoying Liu¹, Weijun Tang¹, Huaming Sun¹, Dong Xue¹, Jianliang Xiao², Chao Wang¹

Affiliations

¹ Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, China.
² Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK.

PMID: 32797653
DOI: 10.1002/anie.202009754

Abstract

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).

Keywords: allylic alcohol; amino alcohol; asymmetric catalysis; hydrogen borrowing; ruthenium catalyst.

Publication types

Research Support, Non-U.S. Gov't