Stereoselective synthesis of phosphoranyl aryloxiranes through the addition of a nucleophilic stable carbene to aromatic aldehydes

Ona Illa, Heinz Gornitzka, Antoine Baceiredo, Guy Bertrand, Vicenç Branchadell, Rosa M. Ortuño

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22 Citations (Scopus)

Abstract

The [2+1] addition of the stable (phosphanyl)(silyl)carbene 1 to aromatic aldehydes affords phosphoranyl aryloxiranes, a new class of polyfunctional epoxides, in high yields and excellent diastereoselectivity. No reaction is observed for aldehydes bearing strongly electron-donating groups. Theoretical calculations show a good correlation between Gibbs activation energy and the electronic nature of the substituent on the phenyl ring.
Original languageEnglish
Pages (from-to)7707-7710
JournalJournal of Organic Chemistry
Volume68
Issue number20
DOIs
Publication statusPublished - 3 Oct 2003

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