Title: A Catalytic Aldol Reacion and Condensation through In Situ Boron “Ate” Complex Enolate Generation in Water

Journal: Angewandte Chemie, International Edition, 2008, Volume 47, Issue 4, pages: 768-770

Authors: Karel Aelvoet, Andrei S. Batsanov, Alexandrea J. Blatch, Christophe Grosjean, Leonard G. F. Patrick, Christian A. Smethurst, Andrew Whiting

DOI: 10.1002/anie.200704293

Cooperation is key: N-Butyl-1-benzimidazole-2-phenylboronic acid hydroxide complex catalyzes the aldol condensation and aldol addition between hydroxyacetone or acetone, and different aldehydes in water. The catalytic activity results from cooperative interactions between the boronate complex and the imidazole function. Aldol condensation gives the unsaturated methyl ketones of acetone, whereas aldol addition predominates with hydroxyacetone.