Enantioselective Michael Addition of Nitromethane to α,β-Enones Catalyzed by Chiral Quaternary Ammonium Salts. A Simple Synthesis of (R)-Baclofen
- 23 November 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (26) , 4257-4259
- https://doi.org/10.1021/ol0068344
Abstract
Enantioselective Michael addition of nitromethane to an α,β-enone is a key step in the synthesis of (R)-baclofen.Keywords
This publication has 19 references indexed in Scilit:
- Highly Enantioselective Michael Reactions Catalyzed by a Chiral Quaternary Ammonium Salt. Illustration by Asymmetric Syntheses of (S)-Ornithine and Chiral 2-CyclohexenonesOrganic Letters, 2000
- 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
- A Critical Analysis of the Mechanistic Basis of Enantioselectivity in the Bis-Cinchona Alkaloid Catalyzed Dihydroxylation of OlefinsJournal of the American Chemical Society, 1996
- Improved enantioselective dihydroxylation of bishomoallylic alcohol derivatives using a mechanistically inspired bis-cinchona alkaloid catalystTetrahedron Letters, 1996
- The stereoselective synthesis of .alpha.-amino acids by phase-transfer catalysisJournal of the American Chemical Society, 1989