Palladium‐Catalyzed Asymmetric Allylic Alkylation of 2,3‐Allenyl Acetates Using a Chiral Diaminophosphine Oxide
- 14 August 2009
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 351 (11-12) , 1773-1778
Abstract
An enantioselective synthesis of allenes through palladium‐catalyzed asymmetric allylic alkylation using a chiral diaminophosphine oxide is described. The asymmetric allylic alkylations proceeded in the presence of a catalytic amount of lithium acetate at 4 °C, affording the chiral allenes in excellent yield with up to 99% ee.Keywords
This publication has 78 references indexed in Scilit:
- Direct and Stereospecific Synthesis of Allenes via Reduction of Propargylic Alcohols with Cp2Zr(H)ClJournal of the American Chemical Society, 2008
- Gold(I)-Catalyzed Intramolecular Hydroarylation of AllenesThe Journal of Organic Chemistry, 2008
- Gold-Catalyzed Highly Enantioselective Synthesis of Axially Chiral AllenesOrganic Letters, 2008
- Gold(I)-Catalyzed Intramolecular Enantioselective Hydroarylation of Allenes with IndolesOrganic Letters, 2007
- Palladium(0)-Catalyzed Synthesis of Chiral Ene-allenes Using Alkenyl TrifluoroboratesThe Journal of Organic Chemistry, 2006
- [2+1] Cycloadditions of Terminal Alkynes to Norbornene Derivatives Catalyzed by Palladium Complexes with Phosphinous Acid LigandsAngewandte Chemie International Edition, 2005
- P-Chirogenic Diaminophosphine Oxide: A New Class of Chiral Phosphorus Ligands for Asymmetric CatalysisJournal of the American Chemical Society, 2004
- Synthese und Eigenschaften allenischer Natur‐ und WirkstoffeAngewandte Chemie, 2004
- Dynamisch‐kinetische Protonierung von racemischen Allenylmetallverbindungen zur asymmetrischen Synthese von AllencarbonsäureesternAngewandte Chemie, 1997
- Axially chiral allenylboranes: catalytic asymmetric synthesis by palladium-catalysed hydroboration of but-1-en-3-ynes and their reaction with an aldehydeJournal of the Chemical Society, Chemical Communications, 1993