Rh-catalyzed formation of dioxolanes from alpha-alkyl diazoesters: diastereoselective cycloadditions of carbonyl ylides with selectivity over beta-hydride elimination |
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| Authors: | DeAngelis Andrew Panne Patricia Yap Glenn P A Fox Joseph M |
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| Institution: | Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. |
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| Abstract: | Described here is a diastereoselective Rh-catalyzed method for the preparation of dioxolanes from alpha-alkyl-alpha-diazoesters. This represents the first general method for generating carbonyl ylides from alpha-diazoesters that possess beta-hydrogens, as such diazo compounds typically give rise to alkenes via beta-hydride elimination. Subsequent cycloaddition with aromatic aldehydes gives tetrasubstituted dioxolanes with unusually high diastereoselectivity. A model is set forth to explain the diastereoselectivity of the cycloaddition. |
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