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Synfacts 2005(2): 0230-0230  
DOI: 10.1055/s-2005-916087
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

1,2-syn Selective and Enantioselective Michael Addition of Propionate Derivatives

Contributor(s): Mark Lautens, Josephine Yuen
T. Harada*, T. Yamauchi, S. Adachi
Kyoto Institute of Technology, Japan
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Publikationsdatum:
25. Oktober 2005 (online)

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Significance

Chiral oxazaborolidine-catalyzed addition of propionate-derived silyl ketene acetals to acyclic enones gave enantioselective and dia­stereoselective (1,2-syn) 1,5-dicarbonyl compounds. The use of 2,6-diisopropylphenol and t-BuOMe as additives were found to enhance the enantioselectivity as they inhibit the racemic pathway catalyzed by Si+ species.