Highly Enantioselective Michael Reactions Catalyzed by a Chiral Quaternary Ammonium Salt. Illustration by Asymmetric Syntheses of (S)-Ornithine and Chiral 2-Cyclohexenones
- 29 March 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (8) , 1097-1100
- https://doi.org/10.1021/ol0056527
Abstract
The use of the chiral quaternary ammonium salts 1a and 1b makes possible enantioselective Michael reactions which have been applied to the asymmetric syntheses of (S)-ornithine (2) and the chiral 2-cyclohexenone 6.Keywords
This publication has 9 references indexed in Scilit:
- Mechanism and Conditions for Highly Enantioselective Epoxidation of α,β-Enones Using Charge-Accelerated Catalysis by a Rigid Quaternary Ammonium SaltOrganic Letters, 1999
- re- andsi-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478)Angewandte Chemie International Edition in English, 1999
- Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalystTetrahedron Letters, 1999
- Highly Enantioselective Phase Transfer Catalyzed Alkylation of a 3-Oxygenated Propionic Ester Equivalent; Applications and MechanismJournal of the American Chemical Society, 1998
- Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalystTetrahedron Letters, 1998
- A Rational Approach to Catalytic Enantioselective Enolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt under Phase Transfer ConditionsJournal of the American Chemical Society, 1997
- Synthesis of L-ornithines stereospecifically deuterated at C-3Tetrahedron Letters, 1993
- The stereoselective synthesis of .alpha.-amino acids by phase-transfer catalysisJournal of the American Chemical Society, 1989
- Mechanism of sodium borohydride-cobaltous chloride reductionsJournal of the American Chemical Society, 1982