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Metal-Free, Mild, Nonepimerizing, Chemo- and Enantio- or Diastereoselective N-Alkylation of Amines by Alcohols via Oxidation/Imine-Iminium Formation/Reductive Amination: A Pragmatic Synthesis of Octahydropyrazinopyridoindoles and Higher Ring Analogues

Imran A. Khan and Anil K. Saxena*

*Laboratory No. 101, Medicinal and Process Chemistry Division (MPC), CSIR-Central Drug Research Institute (CDRI), Chattar Manzil Palace, Lucknow, Uttar Pradesh 226-001, India, Email: ak_saxenacdri.res.in

I. A. Khan, A. K. Saxena, J. Org. Chem., 2013, 78, 11656-11669.

DOI: 10.1021/jo4012249 (free Supporting Information)



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Abstract

An oxidation/imine-iminium formation/reduction cascade using TEMPO-BAIB-HEH-Brønsted acid catalysis in DMPU as solvent enables a mild and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure of amines with alcohols.


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Key Words

reductive amination, amines, iodosobenzene diacetate, TEMPO, Hantzsch ester


ID: J42-Y2013