Iron and Ruthenium Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions between Nitrones and Enals
- 11 April 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (18) , 4968-4969
- https://doi.org/10.1021/ja017814f
Abstract
The single coordination-site transition metal Lewis acids [CpM(BIPHOP-F)][SbF6] (M = Fe, Ru) catalyze the [3+2] dipolar cycloaddition reaction between reactive nitrones and α,β-unsaturated aldehydes to give chiral isoxazolidines with ee values of 75 to >96%. The stereochemistry of the major enantiomer is consistent with an endo approach of the nitrone to the Cα-Si-face of the enal in the s-trans conformation in the (R,R)-catalyst site. The absolute configuration is based on an X-ray structure determination.Keywords
This publication has 4 references indexed in Scilit:
- [(Indenyl)Ru(biphop-F)]+: A Lewis Acid Catalyst That Controls both the Diene and the Dienophile Facial Selectivity in Diels–Alder Reactions This work was supported by the Swiss National Science Foundation (FNS grant 20-59374.99) and The Ministère des Affaires Etrangères from France (Lavoisier grant to V.A.). biphop-F=1,2-bis[bis(pentafluorophenyl)phosphanyloxy]-1,2-diphenylethane.Angewandte Chemie International Edition in English, 2001
- Chiral Cyclopentadienyl-Iron and -Ruthenium Lewis Acids Containing the Electron-Poor BIPHOP-F Ligand: a Comparison as Catalysts in an Asymmetric Diels-Alder ReactionAdvanced Synthesis & Catalysis, 2001
- A Stable and Recoverable Chiral Ru Lewis Acid: Synthesis, Asymmetric Diels–Alder Catalysis and Structure of the Lewis Acid Methacrolein ComplexAngewandte Chemie International Edition in English, 1999
- Control of Diastereo- and Enantioselectivity in Metal-Catalyzed 1,3-Dipolar Cycloaddition Reactions of Nitrones with Alkenes. Experimental and Theoretical InvestigationsThe Journal of Organic Chemistry, 1996