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

Nikolay N. Makukhin; Nataliya S. Goulioukina; Alla G. Bessmertnykh-Lemeune; Stéphane Brandès; Roger Guilard; Irina P. Beletskaya

doi:10.1055/s-0034-1378673

Synthesis, Table of Contents

Synthesis 2015; 47(02): 279-288
DOI: 10.1055/s-0034-1378673

paper

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

Authors

Nikolay N. Makukhin

^aDepartment of Chemistry, Moscow State University, Leninskie Gory, GSP-1, 119991 Moscow, Russian Federation Email: goulioukina@org.chem.msu.ru

^bInstitut 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*

^aDepartment of Chemistry, Moscow State University, Leninskie Gory, GSP-1, 119991 Moscow, Russian Federation Email: goulioukina@org.chem.msu.ru

^cFrumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31, 119071 Moscow, Russian Federation
Alla G. Bessmertnykh-Lemeune*

^bInstitut 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

^bInstitut 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

^bInstitut 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

^aDepartment of Chemistry, Moscow State University, Leninskie Gory, GSP-1, 119991 Moscow, Russian Federation Email: goulioukina@org.chem.msu.ru

^cFrumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31, 119071 Moscow, Russian Federation

Abstract

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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.

Key words

cross-coupling reaction - palladium - cyclopropanes - phosphonates - heterocycles

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References

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