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Synfacts 2010(1): 0028-0028
DOI: 10.1055/s-0029-1218466
DOI: 10.1055/s-0029-1218466
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium-Catalyzed Enantioselective Synthesis of Phthalides
D. H. T. Phan, B. Kim, V. M. Dong*
University of Toronto, Canada
Further Information
Publication History
Publication Date:
21 December 2009 (online)
Significance
The enantioselective synthesis of phthalides 2 via a rhodium-catalyzed intramolecular hydroacylation approach is reported. The appropriate choice of counterion was crucial to avoid decarbonylation and obtain high enantioselectivity. Substrates bearing EDGs and EWGs on the aromatic ring performed equally well in the reaction. However, introduction of a steric bulk ortho to the ketone (R¹ = 3-Me) prohibited the reaction. Variation in the ketone moiety including primary and secondary alkyl groups and electron-rich or electron-deficient aromatics was also tolerated. Excellent enantioselectivities were observed in almost all cases.