Enantio-, Regio- and Chemoselective Copper-Catalyzed 1,2-Hydroborylation of Acylsilanes

Audric Nagy; Laurent Collard; Kiran Indukuri; Tom Leyssens; Olivier Riant

doi:10.1002/chem.201901785

Enantio-, Regio- and Chemoselective Copper-Catalyzed 1,2-Hydroborylation of Acylsilanes

Chemistry. 2019 Jul 2;25(37):8705-8708. doi: 10.1002/chem.201901785. Epub 2019 May 30.

Authors

Audric Nagy¹, Laurent Collard¹, Kiran Indukuri¹, Tom Leyssens¹, Olivier Riant¹

Affiliation

¹ Institute of Condensed Matter and Nanosciences, Molecular Chemistry, Materials and Catalysis (IMCN/MOST), Université catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348, Louvain-la-Neuve, Belgium.

PMID: 31050370
DOI: 10.1002/chem.201901785

Abstract

Enantioselective synthesis of synthetically significant (α-hydroxyallyl)silanes, (α-hydroxyaryl)silanes, and (α-hydroxyalkyl)silanes is reported. The present copper-catalyzed 1,2-selective hydroborylation of acylsilanes affords the aforementioned products in high yields and with high enantiomeric excesses. This robust and scalable additive-free catalytic system relies on the use of low copper(II) acetate and diphosphine ligand loadings at room temperature in the presence of a commercially available and bench-stable hydride source.

Keywords: acylsilane; asymmetric synthesis; copper; hydroborylation; hydroxysilanes.