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The authors thank the Takeda Pharmaceutical Company Limited of Japan (postdoctoral fellowship to M.S.), the California Tobacco-Related Disease Research Program of the University of California, Grant Number 14DT-0004 (predoctoral fellowship to J.L.R.), the NIH-NIGMS (R01 GM 080269-01), and Caltech for financial support, Materia, Inc. for their generous donation of catalyst 9 used in these studies, and Dr. S. Virgil, A. Silberstein, and Y. Segawa for experimental assistance.
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Communication
Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters†
Article first published online: 24 JUL 2008
DOI: 10.1002/anie.200801424
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Seto, M., Roizen, Jennifer L. and Stoltz, Brian M. (2008), Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters. Angew. Chem. Int. Ed., 47: 6873–6876. doi: 10.1002/anie.200801424
- †
Publication History
- Issue published online: 20 AUG 2008
- Article first published online: 24 JUL 2008
- Manuscript Revised: 1 MAY 2008
- Manuscript Received: 25 MAR 2008
Funded by
- California Tobacco-Related Disease Research Program of the University of California. Grant Number: 14DT-0004
- NIH-NIGMS. Grant Number: R01 GM 080269-01
- Caltech
Keywords:
- alcohols;
- allylic compounds;
- asymmetric catalysis;
- enantioselectivity;
- palladium
Adaptive Alkylation: Palladium-catalyzed asymmetric alkylation enables access to fully substituted enantioenriched oxygenated stereocenters, which can be transformed easily to α-hydroxyketones, esters, and acids, providing a catalytic, enantioselective synthesis for natural products.