Asymmetric Cycloadditions of Palladium-Polarized Aza-o-xylylenes
- 6 June 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (26), 8118-8119
- https://doi.org/10.1021/ja801742h
Abstract
Vinyl benzoxazinanones undergo highly enantioselective decarboxylative cycloadditions with electron-deficient olefins in the presence of palladium catalysts. Palladium induces the decarboxylation of the parent benzoxazinanones under mild conditions to produce an intermediate that can be described as a polarized aza-o-xylylene. These intermediates undergo a formal [4 + 2] cycloaddition with good Michael acceptors to produce highly substituted hydroquinolines with excellent regio-, diastereo-, and enantioselectivities.Keywords
This publication has 15 references indexed in Scilit:
- Palladium-Catalyzed Formal [4+2] Cycloaddtion of o-Xylylenes with OlefinsJournal of the American Chemical Society, 2007
- Decarboxylative Ring Contractions and Olefin Insertions of Vinyl OxazinanonesOrganic Letters, 2006
- Palladium(II)-Catalyzed Aerobic Dialkoxylation of Styrenes: A Profound Influence of an o-PhenolJournal of the American Chemical Society, 2006
- Study on supramolecular complexing ability vis-à-vis estimation of pKa of substituted sulfonamides: Dominating role of Balaban index (J)Bioorganic & Medicinal Chemistry Letters, 2005
- “Inverse-Electron-Demand” Ligand Substitution: Experimental and Computational Insights into Olefin Exchange at Palladium(0)Journal of the American Chemical Society, 2004
- Coordination of the Trost modular ligand to palladium allyl fragments: Oligomers, monomers and memory effects in catalysisPublished by Walter de Gruyter GmbH ,2004
- Electrophilicity Parameters for BenzylidenemalononitrilesThe Journal of Organic Chemistry, 2003
- Diels–Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivativesJournal of the Chemical Society, Perkin Transactions 1, 1996
- A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizationsJournal of the American Chemical Society, 1992
- Effect of conformational change on reactivity in organic chemistry. Evaluations, applications, and extensions of Curtin-Hammett Winstein-Holness kineticsChemical Reviews, 1983