Enantioselective thiourea-catalyzed cationic polycyclizations

Robert R. Knowles; Song Lin; Eric N. Jacobsen

doi:10.1021/ja101256v

Enantioselective thiourea-catalyzed cationic polycyclizations

Robert R. Knowles, Song Lin, Eric N. Jacobsen

Research output: Contribution to journal › Article › peer-review

285 Scopus citations

Abstract

A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation?π interactions are a principal determinant of enantioselectivity.

Original language	English (US)
Pages (from-to)	5030-5032
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	132
Issue number	14
DOIs	https://doi.org/10.1021/ja101256v
State	Published - Apr 14 2010
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja101256v

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abstract = "A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation?π interactions are a principal determinant of enantioselectivity.",

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AU - Lin, Song

AU - Jacobsen, Eric N.

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N2 - A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation?π interactions are a principal determinant of enantioselectivity.

AB - A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation?π interactions are a principal determinant of enantioselectivity.

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U2 - 10.1021/ja101256v

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M3 - Article

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JO - Journal of the American Chemical Society

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Enantioselective thiourea-catalyzed cationic polycyclizations

Abstract

All Science Journal Classification (ASJC) codes

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