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_saxena
cdri.res.in
I. A. Khan, A. K. Saxena, J. Org. Chem., 2013, 78, 11656-11669.
DOI: 10.1021/jo4012249
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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
