Synthesis 2015; 47(02): 279-288
DOI: 10.1055/s-0034-1378673
paper
© Georg Thieme Verlag Stuttgart · New York

Exploiting Palladium-Catalyzed Cross-Coupling for the Synthesis of 2-Aryl-Substituted 1-Aminocyclopropylphosphonates

Nikolay N. Makukhin
a   Department of Chemistry, Moscow State University, Leninskie Gory, GSP-1, 119991 Moscow, Russian Federation   eMail: goulioukina@org.chem.msu.ru
b   Institut de Chimie Moléculaire de l’Université de Bourgogne (ICMUB) - UMR 6302 CNRS, 9 Av. Alain Savary, 21000 Dijon, France   eMail: Alla.Lemeune@u-bourgogne.fr
,
Nataliya S. Goulioukina*
a   Department of Chemistry, Moscow State University, Leninskie Gory, GSP-1, 119991 Moscow, Russian Federation   eMail: goulioukina@org.chem.msu.ru
c   Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31, 119071 Moscow, Russian Federation
,
Alla G. Bessmertnykh-Lemeune*
b   Institut de Chimie Moléculaire de l’Université de Bourgogne (ICMUB) - UMR 6302 CNRS, 9 Av. Alain Savary, 21000 Dijon, France   eMail: Alla.Lemeune@u-bourgogne.fr
,
Stéphane Brandès
b   Institut de Chimie Moléculaire de l’Université de Bourgogne (ICMUB) - UMR 6302 CNRS, 9 Av. Alain Savary, 21000 Dijon, France   eMail: Alla.Lemeune@u-bourgogne.fr
,
Roger Guilard
b   Institut de Chimie Moléculaire de l’Université de Bourgogne (ICMUB) - UMR 6302 CNRS, 9 Av. Alain Savary, 21000 Dijon, France   eMail: Alla.Lemeune@u-bourgogne.fr
,
Irina P. Beletskaya
a   Department of Chemistry, Moscow State University, Leninskie Gory, GSP-1, 119991 Moscow, Russian Federation   eMail: goulioukina@org.chem.msu.ru
c   Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31, 119071 Moscow, Russian Federation
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 06. August 2014

Accepted after revision: 07. September 2014

Publikationsdatum:
15. Oktober 2014 (online)


Preview

Abstract

A series of 2-aryl-substituted 1-aminocyclopropylphosphonates containing an additional remote phosphonate group have been synthesized starting from readily accessible dimethyl (1R*,2R*)-2-(4-bromophenyl)-1-formamidocyclopropylphosphonate using cross-coupling methodology. Different types of palladium-catalyzed reactions for carbon–carbon and carbon–phosphorus bond formation were realized. In each case the optimum conditions were found to obtain the desired products in high yield in both small- and large-scale experiments.

Supporting Information