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

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

doi:10.1021/jo200838v

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 journal › Article › peer-review

39 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 language	English (US)
Pages (from-to)	6503-6517
Number of pages	15
Journal	Journal of Organic Chemistry
Volume	76
Issue number	16
DOIs	https://doi.org/10.1021/jo200838v
State	Published - Aug 19 2011
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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.",

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AU - Opalka, Suzanne M.

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AU - Lambiris, Brandon A.

AU - McQuade, D. Tyler

PY - 2011/8/19

Y1 - 2011/8/19

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AB - 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.

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

Abstract

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