Journal
ORGANIC LETTERS
Volume 17, Issue 21, Pages 5160-5163Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02376
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Funding
- NIH-NIGMS [R01GM080269, F32GM073332]
- Amgen
- Gordon and Betty Moore Foundation
- Caltech
- National Cancer Institute of the National Institutes of Health [F31A17435]
- Eli Lilly
- Fannie and John Hertz Foundation
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The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)(3)-t-BuPHOX ligand, alpha-quaternary cyclopentanones were isolated 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 employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.
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