Preparation of α-oxygenated ketones by the dioxygenation of alkenyl boronic acids

Aditi S Patil; Dong-Liang Mo; Heng-Yen Wang; Daniel S Mueller; Laura L Anderson

doi:10.1002/anie.201202704

Preparation of α-oxygenated ketones by the dioxygenation of alkenyl boronic acids

Angew Chem Int Ed Engl. 2012 Jul 27;51(31):7799-803. doi: 10.1002/anie.201202704. Epub 2012 Jun 28.

Authors

Aditi S Patil¹, Dong-Liang Mo, Heng-Yen Wang, Daniel S Mueller, Laura L Anderson

Affiliation

¹ Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St. MC 111, Chicago, IL 60613, USA.

PMID: 22744839
DOI: 10.1002/anie.201202704

Abstract

Two in two: Dioxygenation of alkenyl boronic acids has been achieved with N-hydroxyphthalimide. The two-step process involves etherification of an alkenyl boronic acid with N-hydroxyphthalimide followed by a [3,3] rearrangement. The dioxygenated product can then be hydrolyzed to form either the corresponding α-hydroxy ketone or the α-benzoyloxy ketone.

Publication types

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

MeSH terms

Boronic Acids / chemistry*
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Structure
Oxygen / chemistry*
Stereoisomerism

Substances

Boronic Acids
Ketones
Oxygen