Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 107, Issue 48, Pages 20648-20651Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1002845107
Keywords
asymmetric synthesis; organocatalysis
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Funding
- National Institute of General Medical Sciences [R01 01 GM093213-01]
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The first enantioselective organocatalytic alpha-allylation of cyclic ketones has been accomplished via singly occupied molecular orbital catalysis. Geometrically constrained radical cations, forged from the one-electron oxidation of transiently generated enamines, readily undergo allylic alkylation with a variety of commercially available allyl silanes. A reasonable latitude in both the ketone and allyl silane components is readily accommodated in this new transformation. Moreover, three new oxidatively stable imidazolidinone catalysts have been developed that allow cyclic ketones to successfully participate in this transformation. The new catalyst platform has also been exploited in the first catalytic enantioselective alpha-enolation and alpha-carbooxidation of ketones.
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