One-pot reductive N-alkylation with carbonyl compounds to give tertiary amines via borane reduction of imines

M Tokizane, K Sato, Y Sakami, Y Imori, C Matsuo…

Index: Tokizane, Masashi; Sato, Kaori; Sakami, Yuki; Imori, Yoichiro; Matsuo, Chika; Ohta, Tetsuo; Ito, Yoshihiko Synthesis, 2010 , # 1 p. 36 - 42

Full Text: HTML

Citation Number: 16

Abstract

Abstract One-pot synthesis of tertiary amines via borane-mediated reduction of imines and reductive N-alkylation with carbonyl compounds is described. This protocol's reducing agent is only borane in the reduction of imines, and additional reductant is not necessary in reductive N-alkylation step. When using more than two equivalents of aldehydes, reductive N-alkylation proceeded in good yield.

~99%

~46%

~89%

~89%

~89%

~36%

Synthesis of α, α-dideutero-β-amino esters

[Chandrasekhar; Pendke, Mrunal; Muththe, Chandrashekar; Akondi, Srirama Murthy; Mainkar, Prathama S. Tetrahedron Letters, 2012 , vol. 53, # 10 p. 1292 - 1295]