| Cooperative Thiourea-Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN. | |
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MedLine Citation:
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PMID: 22011108 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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We report a new thiourea-Brønsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and ee´s up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments. |
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Authors:
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Zhiguo Zhang; Katharina M Lippert; Heike Hausmann; Mike Kotke; Peter Richard Schreiner |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-10-19 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 Oct |
Date Detail:
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Created Date: 2011-10-20 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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