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Synfacts 2008(11): 1178-1178
DOI: 10.1055/s-0028-1083441
DOI: 10.1055/s-0028-1083441
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Trapping of an Alcoholic Oxonium Ylide with Aldehydes
X. Zhang, H. Huang, X. Guo, X. Guan, L. Yang, W. Hu*
East China Normal University, Shanghai, Chengdu Institute of Organic Chemistry, and Graduate School of the Chinese Academy of Sciences, Beijing, P. R. of China
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Oktober 2008 (online)

Significance
Previously, the authors have reported a non-enantioselective multicomponent reaction sequence involving trapping of an alcoholic oxonium ylide with aldehydes using Lewis acids. In the present paper the corresponding enantioselective version of this reaction is described through use of a zirconium-binol system developed by Kobayashi. Reactions of aryl diazoacetates, benzyl alcohol, and aromatic aldehydes provide very useful dihydroxylated ester compounds containing an all-carbon stereogenic center in high diastereomeric ratios and enantioselectivities.