Confirmation of the absolute configuration of (−)-aurantioclavine

Handle URI:
http://hdl.handle.net/10754/597830
Title:
Confirmation of the absolute configuration of (−)-aurantioclavine
Authors:
Behenna, Douglas C.; Krishnan, Shyam; Stoltz, Brian M.
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. © 2010 Elsevier Ltd. All rights reserved.
Citation:
Behenna DC, Krishnan S, Stoltz BM (2011) Confirmation of the absolute configuration of (−)-aurantioclavine. Tetrahedron Letters 52: 2152–2154. Available: http://dx.doi.org/10.1016/j.tetlet.2010.11.074.
Publisher:
Elsevier BV
Journal:
Tetrahedron Letters
KAUST Grant Number:
KUS-11-006-02
Issue Date:
Apr-2011
DOI:
10.1016/j.tetlet.2010.11.074
Type:
Article
ISSN:
0040-4039
Sponsors:
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.
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Full metadata record

DC FieldValue Language
dc.contributor.authorBehenna, Douglas C.en
dc.contributor.authorKrishnan, Shyamen
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-25T12:57:26Zen
dc.date.available2016-02-25T12:57:26Zen
dc.date.issued2011-04en
dc.identifier.citationBehenna DC, Krishnan S, Stoltz BM (2011) Confirmation of the absolute configuration of (−)-aurantioclavine. Tetrahedron Letters 52: 2152–2154. Available: http://dx.doi.org/10.1016/j.tetlet.2010.11.074.en
dc.identifier.issn0040-4039en
dc.identifier.doi10.1016/j.tetlet.2010.11.074en
dc.identifier.urihttp://hdl.handle.net/10754/597830en
dc.description.abstractWe 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. © 2010 Elsevier Ltd. All rights reserved.en
dc.description.sponsorshipThis 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.en
dc.publisherElsevier BVen
dc.subjectAbsolute configurationen
dc.subjectAurantioclavineen
dc.subjectAzepinoindoleen
dc.subjectIndole alkaloiden
dc.subjectOxidative kinetic resolutionen
dc.titleConfirmation of the absolute configuration of (−)-aurantioclavineen
dc.typeArticleen
dc.identifier.journalTetrahedron Lettersen
dc.contributor.institutionCalifornia Institute of Technology, Pasadena, United Statesen
dc.contributor.institutionUniversity of California, San Francisco, San Francisco, United Statesen
kaust.grant.numberKUS-11-006-02en
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