메뉴 건너뛰기




Volumn 47, Issue 44, 2008, Pages 8460-8463

Acceptor/acceptor-substituted diazo reagents for carbene transfers: Cobalt-catalyzed asymmetric Z-cyclopropanation of alkenes with a-nitrodiazoacetates

Author keywords

Asymmetric catalysis; Carbenes; Cobalt; Cyclopropanation; Nitroesters; Porphyrinoids

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; COBALT; ENANTIOSELECTIVITY; HYDROCARBONS; OLEFINS; PORPHYRINS; PROPANE;

EID: 54249096882     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803857     Document Type: Article
Times cited : (161)

References (56)
  • 1
  • 4
    • 2142690327 scopus 로고
    • d) J. Salaun, Chem. Rev. 1989, 89, 1247-1270.
    • (1989) Chem. Rev , vol.89 , pp. 1247-1270
    • Salaun, J.1
  • 9
    • 18444417883 scopus 로고
    • e) M. P. Doyle, Chem. Rev. 1986, 86, 919-940.
    • (1986) Chem. Rev , vol.86 , pp. 919-940
    • Doyle, M.P.1
  • 11
    • 54249151100 scopus 로고    scopus 로고
    • For selected examples of asymmetric cyclopropanation with diazocarbonyls, see: Cu-catalyzed systems: a H. Fritschi, U. Leutenegger, A. Pfaltz, Angew. Chem. 1986, 98, 1028-1029;
    • For selected examples of asymmetric cyclopropanation with diazocarbonyls, see: Cu-catalyzed systems: a) H. Fritschi, U. Leutenegger, A. Pfaltz, Angew. Chem. 1986, 98, 1028-1029;
  • 15
    • 0000581242 scopus 로고    scopus 로고
    • Rh-catalyzed systems: d M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen, R. Ghosh, J. Am. Chem. Soc. 1993, 115, 9968-9978;
    • Rh-catalyzed systems: d) M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen, R. Ghosh, J. Am. Chem. Soc. 1993, 115, 9968-9978;
  • 18
    • 0000139463 scopus 로고    scopus 로고
    • Ru-catalyzed systems: g H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224;
    • Ru-catalyzed systems: g) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224;
  • 21
    • 0037119302 scopus 로고    scopus 로고
    • Agnew. Chem. Int. Ed. 2002, 41, 2953-2956;
    • (2002) Agnew. Chem. Int. Ed , vol.41 , pp. 2953-2956
  • 22
    • 33947092924 scopus 로고    scopus 로고
    • Co-catalyzed systems: j A. Nakamura, A. Konishi, Y. Tatsuno, S. Otsuka, J. Am. Chem. Soc. 1978, 100, 3443-3448;
    • Co-catalyzed systems: j) A. Nakamura, A. Konishi, Y. Tatsuno, S. Otsuka, J. Am. Chem. Soc. 1978, 100, 3443-3448;
  • 25
    • 0013152679 scopus 로고    scopus 로고
    • Fe-catalyzed systems: m G. Du, B. Andrioletti, E. Rose, L. K. Woo, Organometallics 2002, 21, 4490-4495.
    • Fe-catalyzed systems: m) G. Du, B. Andrioletti, E. Rose, L. K. Woo, Organometallics 2002, 21, 4490-4495.
  • 33
    • 85152988206 scopus 로고    scopus 로고
    • For other contributions on [Co(Por)]-catalyzed cyclopropanation, see: a) A. Penoni, R. Wanke, S. Tollari, E. Gallo, D. Musella, F. Ragaini, F. Demartin, S. Cenini, Eur. J. Inorg. Chem. 2003, 1452-1460;
    • For other contributions on [Co(Por)]-catalyzed cyclopropanation, see: a) A. Penoni, R. Wanke, S. Tollari, E. Gallo, D. Musella, F. Ragaini, F. Demartin, S. Cenini, Eur. J. Inorg. Chem. 2003, 1452-1460;
  • 35
    • 54249115612 scopus 로고    scopus 로고
    • In addition to the wide substrate scope and high selectivity both diastereo- and enantioselectivity, the CoII-based catalytic system enjoys a practical attribute that is atypical for metal-catalyzed carbene transfers, it can be operated in a one-pot fashion with alkenes as limiting reagents and requires no slow addition of diazo reagents
    • II-based catalytic system enjoys a practical attribute that is atypical for metal-catalyzed carbene transfers - it can be operated in a one-pot fashion with alkenes as limiting reagents and requires no slow addition of diazo reagents.
  • 36
    • 54249149581 scopus 로고    scopus 로고
    • 11], α-nitrodiazoacetates were synthesized on multigram scales and were found to be stable for long storage periods without observation of decomposition or experience of explosion
    • As reported in, may be explosive and should be handled with great care
    • As reported in Ref. [11], α-nitrodiazoacetates were synthesized on multigram scales and were found to be stable for long storage periods without observation of decomposition or experience of explosion. In general, however, diazo reagents may be explosive and should be handled with great care.
    • In general, however, diazo reagents
    • Ref1
  • 47
    • 0034689889 scopus 로고    scopus 로고
    • For selected examples of the use of other acceptor/acceptor-substituted diazo reagents for asymmetric cyclopropanation, see: a M. P. Doyle, S. B. Davies, W. Hu, Org. Lett. 2000, 2, 1145-1147;
    • For selected examples of the use of other acceptor/acceptor-substituted diazo reagents for asymmetric cyclopropanation, see: a) M. P. Doyle, S. B. Davies, W. Hu, Org. Lett. 2000, 2, 1145-1147;
  • 49
    • 0141853181 scopus 로고    scopus 로고
    • For an alternative approach of the use of iodonium ylides to achieve high diastereo- and enantioselectivity, see: a R. P. Wurz, A. B. Charette, Org. Lett. 2003, 5, 2327-2329;
    • For an alternative approach of the use of iodonium ylides to achieve high diastereo- and enantioselectivity, see: a) R. P. Wurz, A. B. Charette, Org. Lett. 2003, 5, 2327-2329;
  • 51
    • 54249088613 scopus 로고    scopus 로고
    • For selected examples of other catalytic asymmetric cyclopropanation reactions that generate highly substituted cyclopropanes, see: a C. D. Papageorgiou, S. V. Ley, M. J. Gaunt, Angew. Chem. 2003, 115, 852-855;
    • For selected examples of other catalytic asymmetric cyclopropanation reactions that generate highly substituted cyclopropanes, see: a) C. D. Papageorgiou, S. V. Ley, M. J. Gaunt, Angew. Chem. 2003, 115, 852-855;
  • 52
    • 0037450150 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 828-831;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 828-831
  • 56
    • 47049124881 scopus 로고    scopus 로고
    • A similar mechanism has been proposed for a nitrene transfer reaction, see
    • A similar mechanism has been proposed for a nitrene transfer reaction, see: J. V. Ruppel, J. E. Jones, C. A. Huff, R. M. Kamble, Y. Chen, X. P. Zhang, Org. Lett. 2008, 10, 1995-1998.
    • (2008) Org. Lett , vol.10 , pp. 1995-1998
    • Ruppel, J.V.1    Jones, J.E.2    Huff, C.A.3    Kamble, R.M.4    Chen, Y.5    Zhang, X.P.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.