4.8 Article

Cr(III)(salen)Cl Catalyzed Enantioselective Intramolecular Addition of Tertiary Enamides to Ketones: A General Access to Enantioenriched 1H-Pyrrol-2(3H)-one Derivatives Bearing a Hydroxylated Quaternary Carbon Atom

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 30, Pages 10390-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja904534t

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Funding

  1. NNSFC [20820102034]
  2. MOST [2006CB806106, 2009CB724704]
  3. CAS

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Catalyzed by a chiral Cr(III)(salen)Cl complex 3e, tertiary enamides 1 underwent an efficient and enantioselective intramolecular addition reaction to an activated carbonyl moiety to produce in excellent yield highly enantioenriched 1H-pyrrol-2(3H)-one derivatives 2 that bear a hydroxylated quaternary carbon atom. The synthetic application of resulting compounds has been demonstrated in the synthesis of (3S,5S)-3,5-diphenyl-3-pyrrolidinol.

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