Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst
Fluor hilft: Ein fluoriertes Triazoliumsalz wurde entwickelt, das als Präkatalysator für die asymmetrische intermolekulare Stetter‐Reaktion von enolisierbaren Aldehyden und Nitrostyrolen dient (siehe Schema). Die trans‐Fluorierung der Katalysatorarchitektur führt zu einer unerreichten Reaktivität un...
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| Published in | Angewandte Chemie Vol. 124; no. 10; pp. 2441 - 2444 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English German |
| Published |
Weinheim
WILEY-VCH Verlag
05.03.2012
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0044-8249 1521-3757 |
| DOI | 10.1002/ange.201107597 |
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| Abstract | Fluor hilft: Ein fluoriertes Triazoliumsalz wurde entwickelt, das als Präkatalysator für die asymmetrische intermolekulare Stetter‐Reaktion von enolisierbaren Aldehyden und Nitrostyrolen dient (siehe Schema). Die trans‐Fluorierung der Katalysatorarchitektur führt zu einer unerreichten Reaktivität und Enantioselektivität in der gewünschten Reaktion. Eine DFT‐Studie liefert Belege für eine elektrostatische Wechselwirkung als die Quelle der gesteigerten Enantioinduktion. |
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| AbstractList | Fluor hilft: Ein fluoriertes Triazoliumsalz wurde entwickelt, das als Präkatalysator für die asymmetrische intermolekulare Stetter‐Reaktion von enolisierbaren Aldehyden und Nitrostyrolen dient (siehe Schema). Die trans‐Fluorierung der Katalysatorarchitektur führt zu einer unerreichten Reaktivität und Enantioselektivität in der gewünschten Reaktion. Eine DFT‐Studie liefert Belege für eine elektrostatische Wechselwirkung als die Quelle der gesteigerten Enantioinduktion. |
| Author | DiRocco, Daniel A. Noey, Elizabeth L. Houk, K. N. Rovis, Tomislav |
| Author_xml | – sequence: 1 givenname: Daniel A. surname: DiRocco fullname: DiRocco, Daniel A. organization: Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA) – sequence: 2 givenname: Elizabeth L. surname: Noey fullname: Noey, Elizabeth L. organization: Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA) – sequence: 3 givenname: K. N. surname: Houk fullname: Houk, K. N. email: houk@chem.ucla.edu organization: Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA) – sequence: 4 givenname: Tomislav surname: Rovis fullname: Rovis, Tomislav email: rovis@lamar.colostate.edu organization: Department of Chemistry, Colorado State University, Fort Collins, CO 80526 (USA) |
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| Copyright | Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Notes | ArticleID:ANGE201107597 NIGMS - No. GM 36700; No. GM 72586 Amgen Roche National Institutes of Health Chemistry-Biology Interface Training Program Grant - No. T32M008496 istex:D7376DB93484EA77F0FECFFDD4F942A221B3C017 National Science Foundation - No. CHE-0548209; No. CHE-0400414 ark:/67375/WNG-5MQ81XVJ-N We thank NIGMS for generous support of this research (GM 36700 to K.N.H. and GM 72586 to T.R.). T.R. thanks Amgen and Roche for unrestricted support. E.L.N. is grateful to the National Institutes of Health Chemistry-Biology Interface Training Program Grant (T32M008496). K.N.H. is grateful to the National Science Foundation (CHE-0548209) for financial support, to the UCLA Academic Technology Services (ATS) Hoffman2 and IDRE clusters for computational resources, and for the TeraGrid resources provided by NCSA (CHE-0400414). We thank NIGMS for generous support of this research (GM 36700 to K.N.H. and GM 72586 to T.R.). T.R. thanks Amgen and Roche for unrestricted support. E.L.N. is grateful to the National Institutes of Health Chemistry‐Biology Interface Training Program Grant (T32M008496). K.N.H. is grateful to the National Science Foundation (CHE‐0548209) for financial support, to the UCLA Academic Technology Services (ATS) Hoffman2 and IDRE clusters for computational resources, and for the TeraGrid resources provided by NCSA (CHE‐0400414). ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
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| References_xml | – reference: Angew. Chem. Int. Ed. 2007, 46, 2988-3000; – reference: Q. Liu, T. Rovis, Org. Lett. 2009, 11, 2856-2859; – reference: L. Hunter, Beilstein J. Org. Chem. 2010, 6, No. 38; – reference: Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215-241; – reference: M. Christmann, Angew. Chem. 2005, 117, 2688-2690; – reference: Angew. Chem. Int. Ed. 2005, 44, 2632-2634; – reference: T. Dudding, K. N. Houk, Proc. Natl. Acad. Sci. USA 2004, 101, 5770-5775; – reference: For a review on the asymmetric intramolecular Stetter reaction, see: J. Read de Alaniz, T. Rovis, Synlett 2009, 1189-1207. – reference: E. Sánchez-Larios, K. Thai, F. Bilodeau, M. Gravel, Org. Lett. 2011, 13, 4942-4945; – reference: D. A. DiRocco, T. Rovis, Angew. Chem. 2011, 123, 8130-8132; – reference: T. Jousseaume, N. E. Wurz, F. Glorius, Angew. Chem. 2011, 123, 1446-1450; – reference: V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995-2001; – reference: Angew. Chem. Int. 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| SubjectTerms | Aldehydes Chemistry Dichtefunktionalrechnungen Fluorierungen N-heterocyclische Carbene Organokatalyse Stetter-Reaktion |
| Title | Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst |
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