Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues
Open Access
- 10 February 2005
- journal article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 3 (6) , 981-984
- https://doi.org/10.1039/b419335k
Abstract
We report the development of a new class of readily prepared chiral 4-(pyrrolidino)-pyridine catalysts capable of exploiting both van der Waals (π) and H-bonding interactions, thus allowing remote chiral information to stereochemically control the kinetic resolution of sec-alcohols.Keywords
This publication has 69 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
- The kinetic resolution of allylic alcohols by a non-enzymatic acylation catalyst; application to natural product synthesisChemical Communications, 2000
- 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
- The Cation−π InteractionChemical Reviews, 1997
- Effective Kinetic Resolution of Secondary Alcohols with a Planar−Chiral Analogue of 4-(Dimethylamino)pyridine. Use of the Fe(C5Ph5) Group in Asymmetric CatalysisJournal of the American Chemical Society, 1997
- Kinetic Resolution of Secondary Alcohols. Enantioselective Acylation Mediated by a Chiral (Dimethylamino)pyridine DerivativeJournal of the American Chemical Society, 1996