Organic Chemistry Portal



Simple One-pot Conversion of Aldehydes and Ketones to Enals

Petr Valenta, Natalie A. Drucker, Jeffrey W. Bode and Patrick J. Walsh*

*P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, Email:

P. Valenta, N. A. Drucker, J. W. Bode, P. J. Walsh, Org. Lett., 2009, 11, 2117-2119.

DOI: 10.1021/ol9005757


A simple and efficient method converts aldehydes into α,β-unsaturated aldehydes with a two-carbon homologation. Hydroboration of ethoxy acetylene with BH3 • SMe2 generates tris(ethoxyvinyl) borane. Transmetalation with diethylzinc, addition to aldehydes or ketones, and acidic workup affords enals or protected derivatives depending on the workup procedure.

see article for more examples

Key Words

Enals, Borane, Hydroboration

ID: J54-Y2009-1510