Confirmation of the absolute configuration of (-)-aurantioclavine
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.
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.
Supplemental Material - mmc1.zip