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A Catalytic Aldol Reaction and Condensation through In Situ Boron “Ate” Complex Enolate Generation in Water
Author(s) -
Aelvoet Karel,
Batsanov Andrei S.,
Blatch Alexandrea J.,
Grosjean Christophe,
Patrick Leonard G. F.,
Smethurst Christian A.,
Whiting Andrew
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200704293
Subject(s) - aldol condensation , aldol reaction , chemistry , acetone , imidazole , phenylboronic acid , organic chemistry , catalysis , boron
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.