Jeremy Steinbacher - Thiourea/Proline Derivative-Catalyzed Synthesis of Tetrahydrofuran Derivatives: A Mechanistic View

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      Publication Details (including relevant citation   information): Opalka, Suzanne M., Steinbacher, Jeremy   L., Lambiris, Brandon A., McQuade, D. Tyler, J. Org.   Chem., 2011, 76 (16), pp 6503-6517

      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.

      Address (URL): http://dx.doi.org/10.1021/jo200838v