Scaffolding Catalysts: Highly Enantioselective Desymmetrization Reactions

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 Vol. 50; no. 35; pp. 8167 - 8171
Main Authors: Sun, Xixi, Worthy, Amanda D., Tan, Kian L.
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 22-08-2011
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Edition:International ed. in 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.
Bibliography:ACS-PRF - No. DNI-5001400
istex:65177C3E4619EFF4830A2F20AE2C1E8FDEB167CA
NIGMS - No. RO1GM087581
ArticleID:ANIE201103470
We thank Professors Marc Snapper and Amir Hoveyda for helpful discussions. We thank Bo Li for X-ray structure analysis of 6. We thank the ACS-PRF (DNI-5001400) and NIGMS (RO1GM087581) for funding this research. Mass spectrometry instrumentation at Boston College is supported by funding from the NSF (DBI-0619576).
ark:/67375/WNG-K65NX28K-L
We thank the ACS‐PRF (DNI‐5001400) and NIGMS (RO1GM087581) for funding this research. Mass spectrometry instrumentation at Boston College is supported by funding from the NSF (DBI‐0619576).
6.
We thank Professors Marc Snapper and Amir Hoveyda for helpful discussions. We thank Bo Li for X‐ray structure analysis of
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201103470