Thiourea/proline derivative-catalyzed synthesis of tetrahydrofuran derivatives: A mechanistic view

Suzanne M. Opalka, Jeremy L. Steinbacher, Brandon A. Lambiris, D. Tyler McQuade

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

A thiourea/proline derivative-catalyzed synthesis of linear α-substituted tetrahydrofuran/pyran derivatives starting with lactol substrates is presented. This study demonstrates the utility and potential complications of using (thio)urea/proline cocatalysis as each of these catalysts is necessary to provide the observed reactivity, but a time-dependent decrease in enantioselectivity is observed. New mechanistic insights into (thio)urea/proline cocatalysis are presented.

Original languageEnglish (US)
Pages (from-to)6503-6517
Number of pages15
JournalJournal of Organic Chemistry
Volume76
Issue number16
DOIs
StatePublished - Aug 19 2011
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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