Palladium-Catalyzed Enantioselective Diboration of Prochiral Allenes
Top Cited Papers
- 24 November 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (50) , 16328-16329
- https://doi.org/10.1021/ja044167u
Abstract
Pd-catalyzed diboration of prochiral allenes occurs exclusively at the internal position and is remarkably accelerated in the presence of Lewis basic ligand structures. On the basis of preliminary observations, a chiral ligand was employed, and the enantiomeric excess of a variety of diboration products was found to be in the range of 86-92% ee. The chiral diboron reaction products should be useful in organic synthesis, and preliminary experiments suggest that they may participate in allylation reactions with a high level of chirality transfer.Keywords
This publication has 18 references indexed in Scilit:
- Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation ReactionOrganic Letters, 2003
- Enantioface-Selective Palladium-Catalyzed Silaboration of Allenes via Double Asymmetric InductionJournal of the American Chemical Society, 2003
- Rhodium-Catalyzed Enantioselective Diboration of Simple AlkenesJournal of the American Chemical Society, 2003
- Palladium-catalysed borylsilylation and borylstannylative dimerization of 1,2-dienesChemical Communications, 1999
- Platinum(0)-catalyzed diboration of allenes with bis(pinacolato)diboronTetrahedron Letters, 1998
- Why Do Pt(PR3)2 Complexes Catalyze the Alkyne Diboration Reaction, but Their Palladium Analogues Do Not? A Density Functional StudyOrganometallics, 1998
- Reaction of BX2−BX2 (X = H or OH) with M(PH3)2 (M = Pd or Pt). A Theoretical Study of the Characteristic FeaturesInorganic Chemistry, 1997
- Transition Metal Catalyzed Diboration of VinylarenesAngewandte Chemie International Edition in English, 1995
- Reactivity of Organoplatinum Complexes with C6H4O2B-BO2C6H4: Syntheses of a Platinum Diboryl Complex with, and without, Metathesis of Boron-Boron and Metal-Carbon BondsJournal of the American Chemical Society, 1995
- The development of a simple general procedure for synthesis of pure enantiomers via chiral organoboranesAccounts of Chemical Research, 1988