Broad-Spectrum Enantioselective Diels−Alder Catalysis by Chiral, Cationic Oxazaborolidines
Top Cited Papers
- 1 August 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (34) , 9992-9993
- https://doi.org/10.1021/ja027468h
Abstract
The cationic chiral Lewis acids 1 and 2, generated by triflic acid protonation of the corresponding neutral oxazaborolidines, serve as excellent catalysts for Diels−Alder addition of cyclopentadiene to a wide variety of dienophiles. Adducts have been obtained in excellent yield and enantioselectivity from α,β-unsaturated esters, lactones, and cyclic ketones. The absolute facial selectivity for each of these substrates follows a common pattern which differs from that observed with α,β-enals. The different reaction channels can be understood in terms of pathways via complexes 3 (for α,β-enals) and 4 (for α,β-enones and esters).Keywords
This publication has 8 references indexed in Scilit:
- Catalytic Enantioselective Diels-Alder Reactions: Methods, Mechanistic Fundamentals, Pathways, and ApplicationsAngewandte Chemie International Edition in English, 2002
- Design and Development of Highly Effective Lewis Acid Catalysts for Enantioselective Diels−Alder ReactionsJournal of the American Chemical Society, 2002
- Asymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral OxazaborolidineJournal of the American Chemical Society, 2002
- The First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated KetonesJournal of the American Chemical Society, 2002
- The formyl C–H⋯O hydrogen bond as a critical factor in enantioselective Lewis-acid catalyzed reactions of aldehydesChemical Communications, 2001
- Catalytic Enantioselective Diels−Alder Reactions of 1,4-Quinone MonoketalsOrganic Letters, 2001
- A Novel Chiral Super-Lewis Acidic Catalyst for Enantioselective SynthesisJournal of the American Chemical Society, 1996
- Two-point-binding asymmetric Diels-Alder catalysts: aromatic alkyldichloroboranesJournal of the American Chemical Society, 1991