Tin(II) Compounds as Catalysts
for the Kabachnik-Fields Reaction under Solvent-Free
Conditions: Facile Synthesis of α-Aminophosphonates

Ricardo Gallardo-Macias; Kensaku Nakayama

doi:10.1055/s-0029-1217091

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Synthesis 2010(1): 57-62
DOI: 10.1055/s-0029-1217091

PAPER

Tin(II) Compounds as Catalysts for the Kabachnik-Fields Reaction under Solvent-Free Conditions: Facile Synthesis of α-Aminophosphonates

Ricardo Gallardo-Macias, Kensaku Nakayama*
Department of Chemistry and Biochemistry, California State University, Long Beach, 1250 Bellflower Blvd., Long Beach, CA 90840, USA
Fax: +1(562)9858557; e-Mail: nakayama@csulb.edu;

Further Information

Publication History

Received 13 July 2009
Publication Date:
26 October 2009 (online)

Abstract
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Abstract

In the presence of a catalytic amount of tin(II) salts, the three-component Kabachnik-Fields reaction involving aldehydes, amines, and diethyl phosphite proceeded smoothly to afford the corresponding α-aminophosphonates in good to high yields. These reactions were carried out under solvent-free conditions.

Key words

α-aminophosphonates - catalysis - imines - Lewis acids - solvent-free

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Lewis acids such as SnCl₂ may not be necessary in the formation of aminophosphonate 3f, which involves piperidine, a secondary aliphatic amine. We are currently investigating the synthesis of α-aminophosphonates from secondary aliphatic amines.