메뉴 건너뛰기




Volumn 14, Issue 22, 2008, Pages 6771-6779

New insights on the mechanism of the transition-metal stereoselective olefin cyclopropanation

Author keywords

Cyclopropanation; Metallocarbenoids; Reaction mechanisms; Stereoselectivity; Transition metals

Indexed keywords

CARBOXYLATION; ELECTRIC NETWORK ANALYSIS; ESTERS; HYDROCARBONS; OLEFINS; ORGANIC COMPOUNDS; STEREOSELECTIVITY; SULFUR COMPOUNDS; TRANSITION METALS;

EID: 53849100313     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800305     Document Type: Article
Times cited : (37)

References (89)
  • 1
    • 1842483218 scopus 로고    scopus 로고
    • For recent reviews: a
    • For recent reviews: a) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382;
    • (2004) Chem. Rev , vol.104 , pp. 1317-1382
    • Diver, S.T.1    Giessert, A.J.2
  • 2
    • 27744492121 scopus 로고    scopus 로고
    • b) C. Bruneau, Angew. Chem. 2005, 117, 2380-2386;
    • (2005) Angew. Chem , vol.117 , pp. 2380-2386
    • Bruneau, C.1
  • 3
    • 18044386806 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2328-2334;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 2328-2334
  • 5
    • 33746305520 scopus 로고    scopus 로고
    • Z. Gu, Angew. Chem. 2006, 118, 206-209;
    • (2006) Angew. Chem , vol.118 , pp. 206-209
    • Gu, Z.1
  • 6
    • 33745446200 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 200-203;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 200-203
  • 8
    • 34250736234 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4042-4059.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4042-4059
  • 12
    • 34250824768 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 3410-3449
  • 14
    • 34547510627 scopus 로고    scopus 로고
    • e) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211.
    • (2007) Chem. Rev , vol.107 , pp. 3180-3211
    • Hashmi, A.S.K.1
  • 17
    • 3242741475 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2402-2406
  • 19
    • 25844453872 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6146-6148.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6146-6148
  • 28
    • 33746216354 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 2901-2904.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 2901-2904
  • 34
    • 0038665161 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1800-1810;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1800-1810
  • 38
    • 24744464788 scopus 로고    scopus 로고
    • For related cyclizations to form indenes, although through [3,3]-sigmatropic rearrangement of the ester, see;
    • a) B. A. Bhanu Prasad, F. K. Yoshimoto, R. Sarpong, J. Am. Chem. Soc. 2005, 127, 12468-12469. For related cyclizations to form indenes, although through [3,3]-sigmatropic rearrangement of the ester, see;
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 12468-12469
    • Bhanu Prasad, B.A.1    Yoshimoto, F.K.2    Sarpong, R.3
  • 40
    • 33746275648 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 3647-3650.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3647-3650
  • 48
    • 0038222536 scopus 로고    scopus 로고
    • For a review of enantioselective cyclopropanation. see;
    • For a review of enantioselective cyclopropanation. see; H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050.
    • (2003) Chem. Rev , vol.103 , pp. 977-1050
    • Lebel, H.1    Marcoux, J.-F.2    Molinaro, C.3    Charette, A.B.4
  • 51
    • 0000531610 scopus 로고    scopus 로고
    • Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer. Berlin
    • a) A. B. Charette, H. Lebel, In Comprehensive Asymmetric Catalyst, Vol. 2 (Eds.; E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer. Berlin. 1999, pp. 581-603;
    • (1999) Comprehensive Asymmetric Catalyst , vol.2 , pp. 581-603
    • Charette, A.B.1    Lebel, H.2
  • 53
    • 53849142953 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 57
    • 84943002905 scopus 로고    scopus 로고
    • 1 salts as a catalyst, see; a H. Schlossarczyk, W. Sieber, M. Hesse, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1973, 56, 875-944;
    • 1 salts as a catalyst, see; a) H. Schlossarczyk, W. Sieber, M. Hesse, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1973, 56, 875-944;
  • 61
    • 4544333104 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 2280-2282.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2280-2282
  • 62
    • 1642264283 scopus 로고    scopus 로고
    • 2 as a catalyst, see; N. Cadran, K. Cariou, G. Hervé, C. Aubert, L. Fensterbank, M. Malacria, J. Marco-Contelles, J. Am. Chem. Soc. 2004, 126, 3408-3409.
    • 2 as a catalyst, see; N. Cadran, K. Cariou, G. Hervé, C. Aubert, L. Fensterbank, M. Malacria, J. Marco-Contelles, J. Am. Chem. Soc. 2004, 126, 3408-3409.
  • 63
    • 38349177267 scopus 로고    scopus 로고
    • 3 as catalysts, see; X. Moreau, J. -P. Goddard, M. Bernard, G. Lemière, J. M. López-Romero, E. Mainetti, N. Marion, V. Mouriès, S. Thorimbert, L. Fensterbank, M. Malacria, Adv. Synth. Catal. 2008, 350, 43-48.
    • 3 as catalysts, see; X. Moreau, J. -P. Goddard, M. Bernard, G. Lemière, J. M. López-Romero, E. Mainetti, N. Marion, V. Mouriès, S. Thorimbert, L. Fensterbank, M. Malacria, Adv. Synth. Catal. 2008, 350, 43-48.
  • 64
    • 53849145390 scopus 로고    scopus 로고
    • For Cu. see ref. [27d].
    • For Cu. see ref. [27d].
  • 65
  • 77
    • 53849133499 scopus 로고    scopus 로고
    • Other effects that have steric and electronic influence in determining the most-favored acyl-shift mode are the substitution at the propargylic site and the catalyst ligands
    • Other effects that have steric and electronic influence in determining the most-favored acyl-shift mode are the substitution at the propargylic site and the catalyst ligands.
  • 79
    • 38349014690 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 718-721.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 718-721
  • 80
    • 53849139819 scopus 로고    scopus 로고
    • Gaussian 03, Revision B.03, M. J. Frisch et al., Gaussian, Inc., Wallingford CT, 2003, See Supporting Information.
    • Gaussian 03, Revision B.03, M. J. Frisch et al., Gaussian, Inc., Wallingford CT, 2003, See Supporting Information.
  • 82


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.