4.6 Article

Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N-Alkyl β-Enamino Esters with Trichlorosilane and Water

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 10, Pages 2846-2848

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201003105

Keywords

amino esters; asymmetric reduction; enantioselectivity; organocatalysis; trichlorosilane

Funding

  1. National Science Foundation of China [20732006, 20972152]
  2. National Key Program of China [2009ZX09501-015]

Ask authors/readers for more resources

First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl beta-enamino esters 1 to give N-alkyl beta-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).

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