Synfacts 2009(7): 0783-0783  
DOI: 10.1055/s-0029-1217261
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Simple One-Pot Conversion of Aldehydes and Ketones into Enals

Contributor(s): Paul Knochel, Andreas J. Wagner
P. Valenta, N. A. Drucker, J. W. Bode, P. J. Walsh*
University of Pennsylvania, Philadelphia, USA
Further Information

Publication History

Publication Date:
22 June 2009 (online)

Significance

The hydroboration of ethoxyacetylene with borane-dimethyl sulfide complex and subsequent transmetalation with diethylzinc provides after reaction with aldehydes or ketones and acidic workup the corresponding C2-homologated α,β-unsaturated aldehydes in high yields. Alternatively, the one-pot workup using either anilinium hydrochloride, ethane-1,2-dithiol or acetic anhydride gives the unsaturated imine, dithiolane or gem-diacetate, respectively.