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Cross‐Coupling Reactions between α , β ‐Unsaturated Ketones and Aldehydes with CrCl 2 : Aldol Condensation and Cyclopropanol Formation
Author(s) -
Toratsu Chika,
Fujii Takafumi,
Suzuki Takuma,
Takai Kazuhiko
Publication year - 2000
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 - 10.1002/1521-3773(20000804)39:15<2725::aid-anie2725>3.0.co;2-u
Subject(s) - aldol condensation , aldol reaction , chemistry , condensation , coupling reaction , coupling (piping) , aldehyde , photochemistry , organic chemistry , materials science , catalysis , physics , metallurgy , thermodynamics
In an aprotic solvent , dimethylformamide, a coupling reaction between an α , β ‐unsaturated ketone and an aldehyde is achieved with chromium( II ) chloride. An intermolecular aldol reaction and an intramolecular cyclization proceed sequentially to give cis ‐2‐hydroxyalkyl‐substituted cyclopropanol stereoselectively [Eq. (a)].