Titanium-catalyzed cyclopropanation of Boc-protected cyanohydrins: A short access to aminocyclopropanecarboxylic acid derivatives

Synthesis

Volumn , Issue 20, 2010, Pages 3410-3414

  Pearson Long, Morwenna S M ^a   Beauseigneur, Alice ^a   Karoyan, Philippe ^b   Szymoniak, Jan ^c   Bertus, Philippe ^a  

^a UNIVERSITÉ DU MAINE   (France)

^b Centre National de la Recherche Scientifique   (France)

^c UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

amino acids; cyanohydrins; cyclopropane; organometallic reagents; titanium

Indexed keywords

ACID DERIVATIVE; CYANOHYDRINS; CYCLOPROPANATION; CYCLOPROPANE; DIASTEREOSELECTIVE SYNTHESIS; ORGANOMETALLIC REAGENTS; STARTING MATERIALS;

AMINO ACIDS; CATALYSIS; ORGANOMETALLICS; PROPANE;

TITANIUM;

1 AMINOCYCLOPROPANECARBOXYLIC ACID; AMINOCYCLOPROPANECARBOXYLIC ACID DERIVATIVE; CYANOHYDRIN; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; TITANIUM; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL MODIFICATION; CYCLOPROPANATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SHORT SURVEY; STEREOCHEMISTRY; SYNTHESIS;

EID: 77957797093     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258260     Document Type: Short Survey

References (41)

1. Reviews for ACC and derivatives:, Brackmann F, deMeijere A, Chem. Rev. 2007 107 4493
2. Cativiela C, Diaz-de-Villegas M D., Tetrahedron: Asymmetry 2000 11 645
3. Burgess K, Ho K K., Moye-Sherman D, Synlett 1994 575
4. Alami A, Calmes M, Daunis J, Jacquier R, Bull. Soc. Chim. Fr. 1993 130 5
5. Yang S F., Hoffman N E., Annu. Rev. Plant Physiol. 1984 35 155
6. Pirrung M C., Acc. Chem. Res. 1999 32 711
7. Nadler V, Kloog Y, Sokolovsky M, Eur. J. Pharmacol. 1988 157 115
8. Trullas R, Folio T, Young A, Miller R, Boje K, Skolnick P, Eur. J. Pharmacol. 1991 203 379
9. See for instance:, Crisma M, Bonora G M., Toniolo C, Barone V, Benedetti E, DiBlasio B, Pavone V, Pedone C, Santini A, Fraternali F, Bavoso A, Lelj F, Int. J. Biol. Macromol. 1989 11 345
10. Evans M C., Pradhan A, Venkatraman S, Ojala W H., Gleason W B., Mishra R K., Johnson R L., J. Med. Chem. 1999 42 1441
11. Zanuy D, Ballano G, Jiménez A I., Casanovas J, Haspel N, Cativiela C, Curcó D, Nussinov R, Alemán C, J. Chem. Inf. Model. 2009 49 1623
12. See for instance:, Husbands S, Suckling C A., Suckling C J., Tetrahedron 1994 50 9729
13. Fink C A., Qiao Y, Berry C J., Sakane Y, Ghai R D., Trapani A J., J. Med. Chem. 1995 38 5023
14. Poupart M.-A, Cameron D R., Chabot C, Ghiro E, Goudreau N, Goulet S, Poirier M, Tsatrizos Y S., J. Org. Chem. 2001 66 4743
15. See for instance:, Moye-Sherman D, Jin S, Ham I, Lim D, Scholtz J M., Burgess K, J. Am. Chem. Soc. 1998 120 9435
16. Jiménez A I., Marraud M, Cativiela C, Tetrahedron Lett. 2003 44 3147
17. Lamarre D, Anderson P C., Bailey M, Beaulieu P, Bolger G, Bonneau P R., Bös M, Cameron D R., Cartier M, Cordingley M G., Faucher A.-M, Coudreau N, Kawai S H., Kukolj G, Lagacé L, LaPlante S R., Narjes H, Poupart M.-A, Rancourt J, Sentjens R E., StGeorge R, Simoneau B, Steinmann G, Thibeault D, Tsantrizos Y S., Weldon S M., Yong C.-L, Llinàs-Brunet M, Nature 2003 426 186
18. Ingold C K., Sako S, Thorpe J F., J. Chem. Soc., Trans. 1922 121 1177
19. Some representative examples for the synthesis of ACC:, King S W., Riordan J M., Holt E M., Stammer C H., J. Org. Chem. 1982 47 3270
20. Cativiela C, Diaz-de-Villegas M D., Jimenez A I., Tetrahedron 1994 50 9157
21. Adlington R M., Aplin R T., Baldwin J E., Rawlings B J., Osborne D, J. Chem. Soc., Chem. Commun. 1982 1086
22. Allwein S P., Secord E A., Martins A, Mitten J V., Nelson T D., Kress M H., Dolling U H., Synlett 2004 2489
23. Hill R K., Prakash S R., Wiesendanger R, Angst W, Martinoni B, Arigoni D, Liu H W., Walsh C T., J. Am. Chem. Soc. 1984 106 795
24. Wheeler T N., Ray J A., Synth. Commun. 1988 18 141
25. Salaün J, Marguerite J, Karkour B, J. Org. Chem. 1990 55 4276
26. Schöllkopf U, Hauptreif M, Dippel J, Nieger M, Egert E, Angew. Chem., Int. Ed. Engl. 1986 25 192
27. Fadel A, Tetrahedron 1991 47 6265
28. Kordes M, Winsel H, deMeijere A, Eur. J. Org. Chem. 2000 3235
29. Bertus P, Szymoniak J, J. Org. Chem. 2002 67 3965
30. Laroche C, Harakat D, Bertus P, Szymoniak J, Org. Biomol. Chem. 2005 3 3482
31. For the synthesis of cyclopropylamines from amides or nitriles, see for amides
32. Chaplinski V, deMeijere A, Angew. Chem., Int. Ed. Engl. 1996 35 413
33. deMeijere A, Kozhushkov S I., Savchenko A I., J. Organomet. Chem. 2004 689 2033
34. Bertus P, Szymoniak J, Chem. Commun. 2001 1792
35. Bertus P, Szymoniak J, J. Org. Chem. 2003 68 7133
36. Bertus P, Szymoniak J, Synlett 2007 1346
37. For the titanium-mediated use of homoallylmagnesium bromide with nitriles, see:, Bertus P, Menant C, Tanguy C, Szymoniak J, Org. Lett. 2008 10 777
38. 13C NMR signals identical to those reported in the literature and proved the unique cis conformation: For cis -methyl ester, see:, Zeng X, Wei X, Farina V, Napolitano E, Xu Y, Zhang L, Haddad N, Yee N K., Grinberg N, Shen S, Senanayaka C H., J. Org. Chem. 2006 71 8864
39. For trans -methyl ester, see:, Beaulieu P L., Gillard J, Bailey M D., Boucher C, Duceppe J.-S, Simoneau B, Wang X.-J, Zhang L, Grozinger K, Houpis I, Farina V, Heimroth H, Krueger T, Schnaubelt J, J. Org. Chem. 2005 70 5869
40. Jiménez J M., Casas R, Ortuño R M., Tetrahedron Lett. 1994 35 5945
41. Fliche C, Braun J, LeGoffic F, Synth. Commun. 1994 24 2873