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Confirmation of the absolute configuration of (-)-aurantioclavine

Behenna, Douglas C. and Krishnan, Shyam and Stoltz, Brian M. (2011) Confirmation of the absolute configuration of (-)-aurantioclavine. Tetrahedron Letters, 52 (17). pp. 2152-2154. ISSN 0040-4039. https://resolver.caltech.edu/CaltechAUTHORS:20110526-081657895

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Abstract

We confirm our previous assignment of the absolute configuration of (−)-aurantioclavine as 7R by crystallographically characterizing an advanced 3-bromoindole intermediate reported in our previous synthesis. This analysis also provides additional support for our model of enantioinduction in the palladium(II)-catalyzed oxidative kinetic resolution of secondary alcohols.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tetlet.2010.11.074 DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403910020848PublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2010 Elsevier Ltd. Available online 18 November 2010. Dedicated to Professor Harry H. Wasserman on behalf of his 90th birthday. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Financial support from Caltech, Amgen, and the California TRDRP (postdoctoral fellowship to S.K.) is also gratefully acknowledged. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased via an NSF CRIF:MU award to Caltech, CHE-0639094.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11-006-02
CaltechUNSPECIFIED
AmgenUNSPECIFIED
California Tobacco-Related Disease Research ProgramUNSPECIFIED
NSF CHE-0639094
Subject Keywords:Aurantioclavine; Absolute configuration; Oxidative kinetic resolution; Indole alkaloid; Azepinoindole
Issue or Number:17
Record Number:CaltechAUTHORS:20110526-081657895
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110526-081657895
Official Citation:Douglas C. Behenna, Shyam Krishnan, Brian M. Stoltz, Confirmation of the absolute configuration of (-)-aurantioclavine, Tetrahedron Letters, Volume 52, Issue 17, Published in honour of Professor Harry H. Wasserman on the occasion of his 90th birthday, 27 April 2011, Pages 2152-2154, ISSN 0040-4039, DOI: 10.1016/j.tetlet.2010.11.074. (http://www.sciencedirect.com/science/article/pii/S0040403910020848)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23803
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 May 2011 15:43
Last Modified:03 Oct 2019 02:50

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