Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones
Robert A. CraigII, Steven A. Loskot, Justin T. Mohr, Douglas C. Behenna, Andrew M. Harned and Brian M. Stoltz*
*California Institute of Technology, MC 101-20, Pasadena,
California 91125, United States, Email: stoltz
caltech.edu
R. A. Craigll, S. A. Loskot, J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Org. Lett., 2015, 17, 5160-5163.
DOI: 10.1021/acs.orglett.5b02376
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Abstract
An enantioselective palladium-catalyzed decarboxylative allylic alkylation enables general enantioselective construction of all-carbon quaternary centers on cyclopentanones in yields up to >99% with ee's up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was developed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.
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Key Words
ID: J54-Y2015
