Control of selectivity in the generation and reactions of oxonium ylides.

Deana M Jaber, Ryan N Burgin, Matthew Hepler, Peter Zavalij, Michael P Doyle

Index: Chem. Commun. (Camb.) 47(27) , 7623-5, (2011)

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Abstract

Dirhodium catalyzed reactions of aryl-substituted tetrahydropyranone diazoacetoacetates produce ylide intermediates that unexpectedly yield two oxabicyclo[4.2.1]-nonane diastereoisomers, but a single diastereoisomer is formed by increasing the steric bulk of the aryl substituent.