Catalytic Asymmetric Reductive Amination of Aldehydes via Dynamic Kinetic Resolution
Top Cited Papers
- 20 September 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (40), 13074-13075
- https://doi.org/10.1021/ja065404r
Abstract
A novel organocatalytic asymmetric reductive amination of aldehydes has been developed. Treating racemic α-branched aldehydes with p-anisidine and a Hantzsch ester in the presence of our previously developed phosphoric acid catalyst, TRIP, gave β-branched secondary amines in excellent yields and enantioselectivities via an efficient dynamic kinetic resolution. The process is applicable to several different aromatic aldehydes and amines but gives slightly reduced enantiomeric ratios with aliphatic aldehydes.Keywords
This publication has 7 references indexed in Scilit:
- Transfer Hydrogenation of α‐Branched Ketimines: Enantioselective Synthesis of Cycloalkylamines via Dynamic Kinetic ResolutionAdvanced Synthesis & Catalysis, 2005
- A Powerful Brønsted Acid Catalyst for the Organocatalytic Asymmetric Transfer Hydrogenation of IminesAngewandte Chemie International Edition, 2005
- Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted AcidAngewandte Chemie International Edition, 2004
- Iminomalonate as a Convenient Electrophilic Amination Reagent for Grignard ReagentsBulletin of the Chemical Society of Japan, 2002
- Stereoselective Organic Synthesis via Dynamic Kinetic ResolutionBulletin of the Chemical Society of Japan, 1995
- Preparation of Ethyl (R)‐(−)‐3‐Hydroxy‐2‐methylpropanoate by Yeast Reduction of Ethyl α‐FormylpropanoateAngewandte Chemie International Edition in English, 1983
- Imine-Enamine Systems and the Mechanism of their Oxidation1Journal of the American Chemical Society, 1956