Scaffolding Catalysts: Highly Enantioselective Desymmetrization Reactions

Ex‐changing places: A highly enantioselective desymmetrization of 1,2‐diols has been developed in which the catalyst utilizes reversible covalent bonding to the substrate to achieve both high selectivity and rate acceleration (see scheme, PMP=pentalmethylpiperidine, TBS=tert‐butyldimethylsilyl). Ind...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-08, Vol.50 (35), p.8167-8171
Main Authors: Sun, Xixi, Worthy, Amanda D., Tan, Kian L.
Format: Article
Language:English
Subjects:
Alcohols - chemistry
asymmetric catalysis
Catalysis
Crystallography, X-Ray
desymmetrization
Molecular Conformation
organocatalysis
Piperidines - chemistry
silanes
Silanes - chemistry
Stereoisomerism
synthetic methods
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Summary:Ex‐changing places: A highly enantioselective desymmetrization of 1,2‐diols has been developed in which the catalyst utilizes reversible covalent bonding to the substrate to achieve both high selectivity and rate acceleration (see scheme, PMP=pentalmethylpiperidine, TBS=tert‐butyldimethylsilyl). Induced intramolecularity is responsible for the enhanced rate, thus allowing the reaction to be performed at room temperature.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201103470