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Confirmation of the absolute configuration of (−)-aurantioclavine
Authors:Douglas C BehennaShyam Krishnan  Brian M Stoltz
Institution:a California Institute of Technology, Division of Chemistry and Chemical Engineering, Mail Code 101-20, Pasadena, CA 91125, USA
b HHMI Institute, University of California, San Francisco, Genentech Hall, 600 16th St, MC 2280, San Francisco, CA 94158, USA
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.
Keywords:Aurantioclavine  Absolute configuration  Oxidative kinetic resolution  Indole alkaloid  Azepinoindole
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