4.8 Article

Asymmetric addition of alpha-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid

Journal

CHEMICAL SCIENCE
Volume 7, Issue 4, Pages 2653-2656

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc04202j

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Funding

  1. NIHGMS [RO1 GM073932]
  2. SIOC
  3. Zhejiang Medicine
  4. Pharmaron
  5. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM073932, R01GM104534] Funding Source: NIH RePORTER

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We describe the asymmetric addition of unactivated alpha-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5- and 1,4-ketoaldehyde derivatives, which are both important building blocks in organic synthesis.

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