Synfacts 2009(4): 0399-0399  
DOI: 10.1055/s-0028-1088137
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palldium-Catalyzed Synthesis of Epoxides by Carboetherification

Contributor(s): Mark Lautens, Praew Thansandote
S. Hayashi, H. Yorimitsu*, K. Oshima*
Kyoto University, Japan
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
23. März 2009 (online)

Significance

A new method for the synthesis of epoxides from tertiary allyl alcohols and aryl halides is reported. The methodology is based on Wolfe’s carboetherification reaction (J. S. Nakhla, J. W. Kampf, J. P. Wolfe J. Am. Chem. Soc. 2006, 128, 2893) and involves the tandem formation of C-C and C-O bonds. The broad scope includes stereoselective versions with dr values in excess of 99:1. For these reactions, the yields and diastereoselectivities increased as bulkier substituents were present on the tertiary alcohol.