Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
Open Access
- 3 December 2015
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 55 (3), 1102-1107
- https://doi.org/10.1002/anie.201508959
Abstract
A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling.Funding Information
- EPSRC
This publication has 91 references indexed in Scilit:
- In situ Catalytic Generation of Allylcopper Species for Asymmetric Allylation: Toward 1H-Isochromene SkeletonsAngewandte Chemie, 2013
- Enantioselective Synthesis of Homoallylic Amines through Reactions of (Pinacolato)allylborons with Aryl-, Heteroaryl-, Alkyl-, or Alkene-Substituted Aldimines Catalyzed by Chiral C1-Symmetric NHC−Cu ComplexesJournal of the American Chemical Society, 2011
- Preparation of Stereodefined Homoallylic Amines from the Reductive Cross-Coupling of Allylic Alcohols with IminesThe Journal of Organic Chemistry, 2010
- syn‐Selective Rhodium(I)‐Catalyzed Allylations of Ketimines Proceeding through a Directed C-H Activation/Allene Addition SequenceAngewandte Chemie, 2010
- Allenamide Hydro−Hydroxyalkylation: 1,2-Amino Alcohols via Ruthenium-Catalyzed Carbonyl anti-AminoallylationOrganic Letters, 2010
- Enantioselective Carbonyl Reverse Prenylation from the Alcohol or Aldehyde Oxidation Level Employing 1,1-Dimethylallene as the Prenyl DonorJournal of the American Chemical Society, 2009
- anti-Aminoallylation of Aldehydes via Ruthenium-Catalyzed Transfer Hydrogenative Coupling of Sulfonamido Allenes: 1,2-AminoalcoholsJournal of the American Chemical Society, 2009
- Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher AldehydesOrganic Letters, 2008
- Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine CatalysisOrganic Letters, 2008
- Moderne Varianten der Mannich-ReaktionAngewandte Chemie, 1998