The Design of NovelN-4‘-Pyridinyl-α-methyl Proline Derivatives as Potent Catalysts for the Kinetic Resolution of Alcohols
- 12 April 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (10) , 3844-3848
- https://doi.org/10.1021/jo026485m
Abstract
A novel family of chiral acylation catalysts based on a N-4‘-pyridinyl-α-methyl proline structure has been studied. A set of 31 compounds has been easily prepared and screened in the kinetic resolution of racemic alcohol 33 resulting in high enantioselectivities in most cases. From results obtained, H-bonding interactions between the catalyst and the substrate would appear essential to afford high enantioselectivity during the catalytic acylation. Additional solvent dependence and anhydride studies have been made to better identify the mechanism. This work has been further extended to the study of a number of structurally different alcohols. Ethanolamine derivatives in particular were found to be highly effective substrates (up to S = 18.8) in the kinetic resolution.Keywords
This publication has 35 references indexed in Scilit:
- Kinetic resolution of amino alcohol derivatives with a chiral nucleophilic catalyst: access to enantiopure cyclic cis-amino alcoholsElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b1/b108753c/Chemical Communications, 2001
- Atropisomeric α-methyl substituted analogues of 4-(dimethylamino)pyridine: synthesis and evaluation as acyl transfer catalystsJournal of the Chemical Society, Perkin Transactions 1, 2001
- Synthesis of C2-symmetric analogues of 4-(pyrrolidino)pyridine: new chiral nucleophilic catalystsJournal of the Chemical Society, Perkin Transactions 1, 2000
- Axially Chiral Analogues of 4-(Dimethylamino)pyridine: Novel Catalysts for Nonenzymatic Enantioselective AcylationsThe Journal of Organic Chemistry, 2000
- Nonenzymatic Kinetic Resolution of Propargylic Alcohols by a Planar−Chiral DMAP Derivative: Crystallographic Characterization of the Acylated Catalyst [J. Am. Chem. Soc. 1999, 121, 5091−5092].Journal of the American Chemical Society, 1999
- Nonenzymatic Kinetic Resolution of Propargylic Alcohols by a Planar−Chiral DMAP Derivative: Crystallographic Characterization of the Acylated CatalystJournal of the American Chemical Society, 1999
- Catalytic Asymmetric Acylation of Racemic Secondary Alcohols with Benzoyl Chloride in the Presence of a Chiral DiamineChemistry Letters, 1999
- Chiral π-Complexes of Heterocycles with Transition Metals: A Versatile New Family of Nucleophilic CatalystsThe Journal of Organic Chemistry, 1996
- Kinetic ResolutionPublished by Wiley ,1988
- 4‐Dialkylaminopyridines as Highly Active Acylation Catalysts. [New synthetic method (25)]Angewandte Chemie International Edition in English, 1978