Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols. (30th September 2020)

• Record Type: Journal Article
• Authors: Xu, Ruirui; Wang, Kun; Liu, Haoying; Tang, Weijun; Sun, Huaming; Xue, Dong; Xiao, Jianliang; Wang, Chao
• Is Part Of: Angewandte Chemie. Volume 132:Number 49(2020)
• Page Start: 22143
• Page End: 22148
• Publication Date: 2020-09-30
• Subjects: allylic alcohol -- amino alcohol -- asymmetric catalysis -- hydrogen borrowing -- ruthenium catalyst; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202009754
• Languages: English
• ISSNs: 0044-8249

Abstract

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 ). Abstract : 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 ).