Issue 27, 2011

Control of selectivity in the generation and reactions of oxonium ylides

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.

Graphical abstract: Control of selectivity in the generation and reactions of oxonium ylides

Supplementary files

Article information

Article type
Communication
Submitted
26 Apr 2011
Accepted
23 May 2011
First published
10 Jun 2011

Chem. Commun., 2011,47, 7623-7625

Control of selectivity in the generation and reactions of oxonium ylides

D. M. Jaber, R. N. Burgin, M. Hepler, P. Zavalij and M. P. Doyle, Chem. Commun., 2011, 47, 7623 DOI: 10.1039/C1CC12443A

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