Use of bifunctional ureas to increase the rate of proline-catalyzed α-aminoxylations

Sarah L. Poe, Andrew R. Bogdan, Brian P. Mason, Jeremy L. Steinbacher, Suzanne M. Opalka, D. Tyler McQuade

Research output: Contribution to journalArticle

43 Scopus citations

Abstract

The rate of the proline-catalyzed α-aminoxylation of aldehydes is significantly increased in the presence of a bifunctional urea. Structure-activity relationship data indicate that both an amine and a urea are crucial for rate enhancement. The evidence presented herein suggests that this rate enhancement originates from the hydrogen bonding interaction between the bifunctional urea and an oxazolidinone intermediate to increase the rate of enamine formation. Proline derivatives that are incapable of forming oxazolidinones exhibit no rate enhancement in the presence of the bifunctional urea. The rate enhancement is general for a variety of aldehydes, and the faster reactions do not reduce yields or selectivities.

Original languageEnglish (US)
Pages (from-to)1574-1580
Number of pages7
JournalJournal of Organic Chemistry
Volume74
Issue number4
DOIs
StatePublished - Feb 20 2009
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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