Stereoselective cyclopropanation of chiral 5-substituted dihydro-2H-piperazines

Tetrahedron Asymmetry

Volumn 24, Issue 1, 2013, Pages 75-79

  Reginato, Gianna ^a   Catalani, Maria Pia ^b   Mordini, Alessandro ^a   Pezzati, Bernardo ^a,b   Bernardelli, Andrea ^b   Davalli, Silvia ^b   Pace, Nicola ^b  

^a ICCOM CNR   (Italy)

^b Aptuit Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-SUBSTITUTED 2,5-DIAZABICYCLO[4.1.0]HEPTANE; 5 SUBSTITUTED DIHYDRO 2H PIPERAZINE DERIVATIVE; HEPTANE DERIVATIVE; PIPERAZINE DERIVATIVE; TERT BUTYL 5 BENZYL 3 (4 BENZYLBENZYL) 2,5 DIAZABICYCLO[4.1.0]HEPTANE 2 CARBOXYLATE; TERT BUTYL 5 BENZYL 3 [(BENZYLOXY)METHYL] 2,5 DIAZABICYCLO[4.1.0]HEPTANE 2 CARBOXYLATE; TERT BUTYL 5 BENZYL 3 ISOBUTYL 2,5 DIAZA BICYCLO[4.1.0]HEPTANE 2 CARBOXYLATE; TERT BUTYL 5 BENZYL 3 ISOPROPYL 2,5 BICYCLO[4.1.0]HEPTANE 2 CARBOXYLATE; TERT BUTYL 5 BENZYL 3 METHYL 2,5 DIAZABICYCLO[4.1.0]HEPTANE 2 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SIMMONS SMITH REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84872296727     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.11.015     Document Type: Article

References (22)

1. B.E. Evans, K.E. Rittle, M.G. Bock, R.M. DiPardo, R.M. Freidinger, W.L. Whitter, G.F. Lundell, D.F. Veber, P.S. Anderson, R.S.L. Chang, V.J. Lotti, D.J. Cerino, T.B. Chen, P.J. Kling, K.A. Kunkel, J.P. Springer, and J. Hirshfield J. Med. Chem. 31 1988 2235
2. K.C. Nicolaou, J.A. Pfefferkorn, A.J. Roecker, G.-Q. Cao, S. Barluenga, and H.J. Mitchell J. Am. Chem. Soc. 122 2000 9939
3. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893
4. M. Vieth, M.G. Siegel, R.E. Higgs, I.A. Watson, D.H. Robertson, K.A. Savin, G.L. Durst, and P.A. Hipskind J. Med. Chem. 47 2004 224
5. T. Miyamota, J. Matsumoto, K. Chiba, H. Egawa, K. Shibamori, A. Minamida, Y. Nishimura, H. Okada, M. Kataoka, M. Fujita, T. Hirose, and J. Nakano J. Med. Chem. 33 1990 1645
6. N. Serradji, O. Bensaid, M. Martin, E. Kan, N.D. Bosquet, C. Redeuilh, J. Huet, F. Heymans, A. Lamouri, P. Clayette, C.Z. Dong, D. Dormont, and J.J. Godfroid J. Med. Chem. 43 2000 2149
7. H.S. Parihar, A. Suryanarayanan, C. Ma, P. Joshi, P. Venkataraman, K.M. Schulte, and K.S. Kirschbaum Bioorg. Med. Chem. Lett. 11 2001 2133
8. D. Giardinh, U. Gulini, M. Massi, M.G. Piloni, P. Pompei, G. Rafaiani, and C. Melchiorre J. Med. Chem. 36 1993 690
9. J.A. Lopez, T. Okayama, K. Hosohata, P. Davis, F. Porreca, H.I. Yamamura, and V.J. Hruby J. Med. Chem. 42 1999 5359
10. A. Naylor, D.E. Judd, J.E. Lloyd, D.I. Scopes, A.G. Hayes, and P.J. Birch J. Med. Chem. 36 1993 2075
11. S. Soukara, C.A. Maier, U. Predoiu, A. Ehret, R. Jackisch, and B. Wünsch J. Med. Chem. 44 2001 2814
12. S. Bedürftig, and B. Wünsch Eur. J. Med. Chem. 41 2006 387
13. R.R.R. Taylor, H.C. Twin, W.W. Wen, R.J. Mallot, A.J. Lough, S.D. Gray-Owen, and R.A. Batey Tetrahedron 66 2010 3370
14. See for instance: S.D. Pol, C. Zorn, C.D. Klein, O. Zerbe, and O. Reiser Angew. Chem., Int. Ed. 43 2004 511
15. See for instance: R.A.J. Casero, and P.M. Woster J. Med. Chem. 52 2009 4551
16. Z. Song, T. Lu, R.P. Hsung, Z.F. Al-Rashid, C. Ko, and Y. Tang Angew. Chem., Int. Ed. 46 2007 4069 and ref. cited
17. G. Reginato, B. Di Credico, D. Andreotti, A. Paio, and D. Donati Tetrahedron: Asymmetry 18 2007 2680
18. G. Reginato, B.D. Credico, D. Andreotti, A. Mingardi, A. Paio, D. Donati, B. Pezzati, and A. Mordini Tetrahedron Asymmetry 21 2010 191
19. H.E. Simmons, and R.D. Smith J. Am. Chem. Soc. 80 1958 5323
20. H. Lebel, J.-F. Marcoux, C. Molinaro, and A.B. Charette Chem. Rev. 103 2003 977
21. L.C. Pattenden, H. Adams, S.A. Smith, and J.P.A. Harrity Tetrahedron 64 2008 2951
22. G. Reginato, B. DiCredico, D. Andreotti, A. Mingardi, A. Paio, and D. Donati Tetrahedron: Asymmetry 18 2007 2680