Abstract
A simple and convenient method was developed for the preparation of hindered tertiary amines via direct reductive amination of ketones with secondary aryl amines, using trichlorosilane as reducing agent and tetramethylethylenediamine (TMEDA) as organic Lewis base activator. A broad range of ketones were reacted with N-methylaniline to afford the corresponding tertiary amine products in high yield. An open transition model was proposed for the reductive step.
Highlights
Tertiary amines are a key structural motif in numerous biologically active natural products such as alkaloids and pharmaceutical molecules
Direct reductive amination (DRA) of carbonyls with amines (Scheme 1) is one of the most convenient and straightforward methods for the synthesis of amines [1–13]. It proceeds in a one-pot fashion under mild conditions and is compatible with many functional groups
We were interested to test if this reduction system could be applicable for the challenging intermolecular DRA
Summary
Department of Pharmaceutics Engineering, Xihua University, Chengdu 610039, China Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China Received: 4 April 2012; in revised form: 25 April 2012 / Accepted: 25 April 2012 /
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