Synthesis of α-Aminocyclopropylphosphonic
Acids

Andrey V. Chemagin; Nikolai V. Yashin; Yuri K. Grishin; Tamara S. Kuznetsova; Nikolai S. Zefirov

doi:10.1055/s-0030-1257865

PAPER

Synthesis of α-Aminocyclopropylphosphonic Acids

Andrey V. Chemagin^a, Nikolai V. Yashin*^a,b, Yuri K. Grishin^a, Tamara S. Kuznetsova^a,b, Nikolai S. Zefirov^a,b
^a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1-3, Moscow 119991, Russian Federation
Fax: +7(495)9393969; e-Mail: yashin-n@org.chem.msu.ru;
^b IPhAC RAS, Severnyi Proezd 1, Chernogolovka, Moscow Region 142432, Russian Federation

Abstract

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Abstract

A convenient, general approach to α-aminocyclopropylphosphonic acids via reduction and hydrolysis of α-nitrocyclopropylphosphonates is described. A number of the title compounds were synthesized in excellent yields.

Key words

aminophosphonic acids - bioisosteres - cyclopropanes - reduction - hydrolysis

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References

1a Sheridan RP. J. Chem. Inf. Comput. Sci. 2002, 42: 103

1b Cammarata A. Menon GK. J. Med. Chem. 1976, 19: 739

1c Patani GA. LaVoie EJ. Chem. Rev. 1996, 96: 3147

2a Ordóñez M. Rojas-Cabrera H. Cativiela C. Tetrahedron 2009, 65: 17

2b Kafarski B. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63: 193

2c Atherton FR. Hassall CH. Lambert RW. J. Med. Chem. 1986, 29: 29

2d Wolfenden R. Annu. Rev. Biophys. Bioeng. 1976, 5: 271

3a Wang P. Brank AS. Banavali NK. Nicklaus MC. Marquez VM. Christman JK. MacKerell AD. J. Am. Chem. Soc. 2000, 122: 12422

3b Hoepping A. Johnson KM. Clifford G. Flippen-Anderson J. Kozikowski AP. J. Med. Chem. 2000, 43: 2064

3c Halab L. Gosselin F. Lubell WD. Biopolymers 2000, 55: 101

3d Pellicciari R. Marinozzi M. Camaioni E. Nunez M. Costantino G. Gasparini F. Giorgi G. Macchiarulo A. Subramanian N. J. Org. Chem. 2002, 67: 5497

3e Brackmann F. de Meijere A. Chem. Rev. 2007, 107: 4493

4a Averina EB. Yashin NV. Kuznetsova TS. Zefirov NS. Vestn. Mosk. Univ., Ser. 2, Khim. 2002, 43: 246 ; Chem. Abstr. 2002, 138, 254854

4b Yashin NV. Averina EB. Gerdov SM. Kuznetsova TS. Zefirov NS. Tetrahedron Lett. 2003, 44: 8241

4c Averina EB. Yashin NV. Shvorina EB. Grishin YuK. Kuznetsova TS. Vestn. Mosk. Univ., Ser. 2, Khim. 2005, 46: 314 ; Chem. Abstr. 2006, 145, 145989

4d Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis 2006, 279

4e Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis 2006, 880

4f Chemagin AV. Yashin NV. Averina EB. Kuznetsova TS. Zefirov NS. Dokl. Akad. Nauk 2008, 419: 772 ; Chem. Abstr. 2009, 150, 121216

5a Yashin NV. Villemson EV. Chemagin AV. Averina EB. Kabachnik MM. Kuznetsova TS. Synthesis 2008, 464

5b Matveeva ED. Podrugina TA. Tishkovskaja EV. Tomilova LG. Zefirov NS. Synlett 2003, 2321

6a Erion MD. Walsh CT. Biochemistry 1987, 26: 3417

6b Groth U. Lehmann L. Richter L. Schöllkopf U. Liebigs Ann. Chem. 1993, 427

6c Yamazaki S. Takada T. Moriguchi Y. Yamabe S. J. Org. Chem. 1998, 63: 5919

6d Fadel A. J. Org. Chem. 1999, 64: 4953

6e Tesson N. Dorigneux B. Fadel A. Tetrahedron: Asymmetry 2002, 13: 2267

7 Chemagin AV. Yashin NV. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis 2010, 259

8 Wurz RP. Charette AB. J. Org. Chem. 2004, 69: 1262