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Volumn 23, Issue 8, 2004, Pages 1918-1927

High Stereoselectivity and Facial Selectivity in Diels-Alder Cycloadditions of Novel Captodative Olefins: α-Alkoxyvinyl(ethoxy)carbene Chromium Complexes with Cyclopentadienes

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL SHIFTS; DIELS ALDER CYCLOADDITIONS; ELECTRONIC EFFECTS; STEREOSELECTIVITY;

EID: 2342429394     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0343317     Document Type: Article
Times cited : (17)

References (75)
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    • Vázquez, M. A.; Cessa, L.; Vega, J. L.; Osorio, L.; Miranda, R.; Tamariz, J.; Delgado, F. Unpublished
    • Vázquez, M. A.; Cessa, L.; Vega, J. L.; Osorio, L.; Miranda, R.; Tamariz, J.; Delgado, F. Unpublished.
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    • (a) Monnin, J. Chimia 1957, 11, 337.
    • (1957) Chimia , vol.11 , pp. 337
    • Monnin, J.1
  • 53
    • 2342424038 scopus 로고    scopus 로고
    • note
    • We attempted to carry out molecular orbital calculations in order to locate the transition states of these reactions. However, even with semiempirical models (PM3) we had problems with the convergence of the wave function. We were unable to carry out any optimizations, even of the products or the carbenes themselves. The drawings that we present here (Figures 2 and 5) were made by molecular mechanics optimization using the Sybyl force field as implemented in the MacSpartan program package. The distances between C-l and C-4 of the cyclopentadienes and C-2 and C-3 of the dienophile were fixed at 2.55 and 1.85 Å, respectively. The figures are only intended to be approximate representations of the real transition states and to show the important interactions involved in determining the stereoselectivity of these processes.
  • 57
    • 2342443246 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 73
    • 0001086706 scopus 로고
    • Kluwer Academic Publishers: Dordrecht, The Netherlands, Table 4.24.2
    • Wilson, A. J. C. International Tables for Crystallography; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995; Vol. C, Table 4.24.2, p 193.
    • (1995) International Tables for Crystallography , vol.100 , pp. 193
    • Wilson, A.J.C.1
  • 75
    • 0004150157 scopus 로고    scopus 로고
    • Siemens Energy & Automation: Germany
    • SHELXTL, v. 5.08; Siemens Energy & Automation: Germany, 1995.
    • (1995) SHELXTL, v. 5.08


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.