4.4 Article

Confirmation of the absolute configuration of (-)-aurantioclavine

Journal

TETRAHEDRON LETTERS
Volume 52, Issue 17, Pages 2152-2154

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.074

Keywords

Aurantioclavine; Absolute configuration; Oxidative kinetic resolution; Indole alkaloid; Azepinoindole

Funding

  1. King Abdullah University of Science and Technology (KAUST) [KUS-11-006-02]
  2. Caltech
  3. Amgen
  4. California TRDRP
  5. NSF [CHE-0639094]

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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. (C) 2010 Elsevier Ltd. All rights reserved.

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