Issue 27, 2011
From the journal:

Chemical Communications

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

Deana M. Jaber,a   Ryan N. Burgin,a   Matthew Hepler,a   Peter Zavalija  and  Michael P. Doyle*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA
E-mail: mdoyle3@umd.edu

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

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Article information

DOI
https://doi.org/10.1039/C1CC12443A
Article type
Communication
Submitted
26 Apr 2011
Accepted
23 May 2011
First published
10 Jun 2011

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

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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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