Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki–Miyaura cross-coupling

Authors

Gia L. Hoang, University of Nebraska-LincolnFollow
James M. Takacs, University of Nebraska-LincolnFollow

ORCID IDs

Gia L. Hoang http://orcid.org/0000-0003-2332-1854

James M. Takacs http://orcid.org/0000-0002-1903-6535

Date of this Version

2017

Citation

Chem. Sci., 2017, 8, 4511–4516

Comments

This Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licence

Abstract

The rhodium-catalyzed, directed catalytic asymmetric hydroboration of γ,δ-unsaturated amides affords a direct route to chiral acyclic secondary γ-borylated carbonyl derivatives in high enantiomeric purity. In contrast to a similar β-borylated amide derivative, the γ-borylated amide undergoes Suzuki–Miyaura cross-coupling with stereoretention. The utility of the boronic ester products is further illustrated by other stereospecific C–B bond transformations leading to γ-amino acid derivatives, 1,4-amino alcohols, and 5-substituted-γ-lactone and γ-lactam ring systems.

Includes Supplementary Materials.