Confirmation of the absolute configuration of (−)-aurantioclavine

Douglas C. Behenna; Shyam Krishnan; Brian M. Stoltz

doi:10.1016/j.tetlet.2010.11.074

Confirmation of the absolute configuration of (−)-aurantioclavine

Douglas C. Behenna, Shyam Krishnan, Brian M. Stoltz

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

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.

Original language	English (US)
Pages (from-to)	2152-2154
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.074
State	Published - Apr 2011
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-11-006-02
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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10.1016/j.tetlet.2010.11.074

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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. {\textcopyright} 2010 Elsevier Ltd. All rights reserved.",

author = "Behenna, {Douglas C.} and Shyam Krishnan and Stoltz, {Brian M.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-11-006-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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doi = "10.1016/j.tetlet.2010.11.074",

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ER -

Confirmation of the absolute configuration of (−)-aurantioclavine

Abstract

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