Organocatalytic Enantioselective Conjugate Addition to Alkynones
- 15 April 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (18), 5672-5673
- https://doi.org/10.1021/ja0493594
Abstract
The first catalytic enantioselective addition of β-dicarbonyl compounds to alkynones is presented. The conjugate addition proceeds in very high yields, giving a mixture of (Z)- and (E)-enones with up to 95% ee using the cinchona alkaloid [DHQ]2PHAL (5 mol %) as the catalyst. This organocatalytic enantioselective reaction has been further developed to a one-pot procedure to give the optically active (E)-enone adduct using first [DHQ]2PHAL (5 mol %), followed by Bu3P (10 mol %), as the catalysts.Keywords
This publication has 4 references indexed in Scilit:
- Formation of Quaternary Stereocenters by Copper‐Catalyzed Michael Reactions with L‐Valine Amides as AuxiliariesChemistry – A European Journal, 2003
- Unusual O-conjugate addition reactions of β-ketoesters and 1,3-diketones to ethyl propynoate: applications to the synthesis of furansTetrahedron Letters, 2003
- Functionalized Cis- and Trans-Fused Bicyclic α-Amino Acids via Stereoselective Double Annulation and Dequaternization ReactionsThe Journal of Organic Chemistry, 2003
- The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched AlcoholsOrganic Letters, 2001