Copper(ii)/amine synergistically catalyzed enantioselective alkylation of cyclic N-acyl hemiaminals with aldehydes
- 21 May 2015
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 51 (53) , 10691-10694
Abstract
The first catalytic asymmetric alkylation of N-acyl quinoliniums with aldehydes has been described. A copper/amine synergistic catalytic system has been developed, allowing the addition of functionalized aldehydes to a wide range of electronically varied N-acyl quinoliniums in good yields with excellent enantiocontrol. The synergistic catalytic system was also effective for N-acyl dihydroisoquinoliniums and β-caboliniums, demonstrating the general applicability of the protocol in the enantioselective alkylation of diverse cyclic N-acyl hemiaminals.Keywords
This publication has 56 references indexed in Scilit:
- Catalytic Asymmetric Addition of Aldehydes to Oxocarbenium Ions: A Dual Catalytic System for the Synthesis of ChromenesOrganic Letters, 2012
- Enantioselective Oxidative Cross‐Dehydrogenative Coupling of Tertiary Amines to AldehydesAngewandte Chemie International Edition, 2012
- Synergistic catalysis: A powerful synthetic strategy for new reaction developmentChemical Science, 2012
- Catalytic Asymmetric Alkynylation of C1‐Substituted C,N‐Cyclic Azomethine Imines by CuI/Chiral Brønsted Acid Co‐CatalystAngewandte Chemie International Edition, 2011
- Cover Picture: Cooperative Catalytic Reactions Using Organocatalysts and Transition-Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes (Angew. Chem. Int. Ed. 40/2010)Angewandte Chemie International Edition, 2010
- The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of AldehydesJournal of the American Chemical Society, 2010
- Enantioselective Aldehyde α-Nitroalkylation via Oxidative OrganocatalysisJournal of the American Chemical Society, 2009
- Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of AldehydesScience, 2008
- Enantioselective Allylzincation of Cyclic Aldimines in the Presence of Anionic Bis-oxazoline LigandJournal of the American Chemical Society, 1996
- Quinoline, quinazoline, and acridone alkaloidsNatural Product Reports, 1995