Counterions of BINAP−Pt(II) and −Pd(II) Complexes: Novel Catalysts for Highly Enantioselective Diels−Alder Reaction
- 1 December 1999
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (13), 2157-2159
- https://doi.org/10.1021/ol990346i
Abstract
Platinum and palladium chiral bisphosphine complexes and their counterion effects in asymmetric Diels−Alder reactions have been investigated. The reaction of cyclopentadiene and various bidentate dienophiles in the presence of a catalytic amount of Pt(II)− or Pd(II)−BINAP complex proceeds with excellent endo/exo selectivity as well as endo enantioselectivity (up to 99% ee).Keywords
This publication has 15 references indexed in Scilit:
- Palladium(II)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Nitrones to 3-Alkenoyl-1,3-oxazolidin-2-onesThe Journal of Organic Chemistry, 1999
- Platinum-Catalyzed Enantioselective Aldol Addition of Ketene Silyl Acetals to AldehydesJournal of the American Chemical Society, 1998
- Platinum-Catalyzed Oxidations with Hydrogen Peroxide: The (Enantioselective) Epoxidation of .alpha.,.beta.-Unsaturated KetonesOrganometallics, 1995
- First Example of a Highly Enantioselective Catalytic Diels-Alder Reaction of an Achiral C2v-Symmetric Dienophile and an Achiral DieneJournal of the American Chemical Society, 1994
- REAGENT-CONTROLLED ASYMMETRIC DIELS-ALDER REACTIONS. A REVIEWOrganic Preparations and Procedures International, 1994
- Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran with phenyl triflate. A novel asymmetric catalysis involving a kinetic resolution processOrganometallics, 1993
- Catalytic asymmetric Diels Alder reactionsChemical Reviews, 1992
- Intermolecular Diels–Alder ReactionsPublished by Elsevier BV ,1991
- Theoretical studies of conformations of acrolein, acrylic acid, methyl acrylate, and their Lewis acid complexesJournal of the American Chemical Society, 1987
- ASYMMETRIC DIELS–ALDER REACTION PROMOTED BY A CHIRAL TITANIUM REAGENTChemistry Letters, 1986