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Synfacts 2009(5): 0512-0512
DOI: 10.1055/s-0029-1216590
DOI: 10.1055/s-0029-1216590
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium-Catalyzed Reductive Coupling of Enones and Aromatic Aldehydes
T. Shiomi, T. Adachi, J.-i. Ito, H. Nishiyama*
Nagoya University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2009 (online)

Significance
As an extension on previous work concerning the reductive coupling of α,β-unsaturated esters with aldehydes or ketones (J. Am. Chem. Soc. 2005, 127, 6972), the authors now describe the rhodium-catalyzed reductive coupling of enones with aromatic aldehydes. The product β-hydroxyketones were obtained with high anti selectivity and enantioselectivity. A cyclic transition state on the rhodium active site is proposed for the reaction, whereby the Re-face of the enolate carbon atom could attack the Re-face of the aldehyde carbon atom leading to the observed stereochemistry.