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Volumn 61, Issue 46, 2005, Pages 10886-10893

Computer-assisted design of asymmetric 1,3-dipolar cycloadditions between dimethylvinylborane and chiral nitrones

Author keywords

1,3 Dipolar cycloadditions; Chiral nitrones; Selectivity; Theoretical study; Vinylboranes

Indexed keywords

BORANE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; NITROGEN; NITRONE; VINYL DERIVATIVE;

EID: 26844496066     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.004     Document Type: Article
Times cited : (6)

References (50)
  • 19
    • 0142258275 scopus 로고    scopus 로고
    • Alkynyl- and vinylboronates have been used as dipolarophiles in the 1,3-dipolar cycloaddition reactions of nitrones and nitrile N-oxides. However, it has been shown that the reactivity and selectivity pattern of these boron-activated dipolarophiles is significantly influenced by the oxygen atoms attached to the boron. Preliminary DFT calculations performed in our group suggest the lower electrophilic character of the boron atom relative to their dialkyl counterparts affects the potential energy surfaces to a great extent, making these cycloadditions become classical [3+2] processes. For a related DFT study see: (a) J.A. Sáez, M. Arnó, and L.R. Domingo Tetrahedron 59 2003 9167 9171
    • (2003) Tetrahedron , vol.59 , pp. 9167-9171
    • Sáez, J.A.1    Arnó, M.2    Domingo, L.R.3
  • 40
    • 0345887443 scopus 로고    scopus 로고
    • Schrodinger, Inc., Portland, Oregon
    • Jaguar 4.2, Schrodinger, Inc., Portland, Oregon, 2002.
    • (2002) Jaguar 4.2
  • 41
    • 0037111678 scopus 로고    scopus 로고
    • We have come across similar findings when studying the Diels-Alder reactions of alkynylboranes, which makes us believe this behavior could be related to a bifurcation in the potential energy surface. (a) M.A. Silva, S.C. Pellegrinet, and J.M. Goodman J. Org. Chem. 67 2002 8203 8209
    • (2002) J. Org. Chem. , vol.67 , pp. 8203-8209
    • Silva, M.A.1    Pellegrinet, S.C.2    Goodman, J.M.3
  • 43
    • 26844566777 scopus 로고    scopus 로고
    • note
    • We followed Rastelli's nomenclature for the regiochemistry (A and B pathways generate 4- and 5-borylisoxazolidines, respectively).
  • 44
    • 26844556509 scopus 로고    scopus 로고
    • note
    • This observation suggests the conclusions drawn with prototype compounds may not be completely valid for real systems and highlights the importance of the model chosen for performing computational studies.
  • 49
    • 0001161818 scopus 로고    scopus 로고
    • Several conformational switches in transition structures have been described for other cycloaddition reactions. For example, see: J. Liu, S. Niwayama, Y. You, and K.N. Houk J. Org. Chem. 63 1998 1064 1073
    • (1998) J. Org. Chem. , vol.63 , pp. 1064-1073
    • Liu, J.1    Niwayama, S.2    You, Y.3    Houk, K.N.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.