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Volumn 44, Issue 10, 2005, Pages 1513-1517

Bromoallenes as allyl dication equivalents in the absence of palladium(0): Synthesis of bicyclic sulfamides by tandem cyclization of bromoallenes

Author keywords

Allenes; Cyclization; Halogen compounds; Palladium; Sulfamides

Indexed keywords

ATOMS; CARBON; NITROGEN; PALLADIUM COMPOUNDS; SULFAMIC ACID; SYNTHESIS (CHEMICAL);

EID: 16244407181     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462557     Document Type: Article
Times cited : (49)

References (46)
  • 1
    • 16244408580 scopus 로고    scopus 로고
    • (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim
    • S. Ma, in Modern Allene Chemistry, Vol. 2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, pp. 614-619.
    • (2004) Modern Allene Chemistry , vol.2 , pp. 614-619
    • Ma, S.1
  • 5
    • 0038076018 scopus 로고    scopus 로고
    • a) H. Ohno, H. Hamaguchi, M. Ohata, T. Tanaka, Angew. Chem. 2003, 115, 1791-1795; Angew. Chem. Int. Ed. 2003, 42, 1749-1753;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1749-1753
  • 32
    • 0011133965 scopus 로고
    • a) M. Preiss, Chem. Ber. 1978, 111, 1915-1921;
    • (1978) Chem. Ber. , vol.111 , pp. 1915-1921
    • Preiss, M.1
  • 34
    • 0042034174 scopus 로고    scopus 로고
    • New methods for the synthesis of cyclosulfamides have been reported recently. For the synthesis of five-membered cyclosulfamides starting from amino acids, see: c) Z. Regaïnia, M. Abdaoui, N.-E. Aouf, G. Dewynter, J.-L. Montero, Tetrahedron 2000, 56, 381-387.
    • (2000) Tetrahedron , vol.56 , pp. 381-387
    • Regaïnia, Z.1    Abdaoui, M.2    Aouf, N.-E.3    Dewynter, G.4    Montero, J.-L.5
  • 36
    • 0037131479 scopus 로고    scopus 로고
    • For the synthesis of nonsymmetrical sulfamides using Burgess-type reagents, see: d) K. C. Nicolaou, D. A. Longbottom, S. A. Snyder, A. Z. Nalbanadian, X. Huang, Angew. Chem. 2002, 114, 4022-4026; Angew. Chem. Int. Ed. 2002, 41, 3866-3870.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3866-3870
  • 42
    • 16244385564 scopus 로고    scopus 로고
    • note
    • N2′-type, intramolecular nucleophilic attack on the proximal carbon of the allene moiety.
  • 43
    • 16244378824 scopus 로고    scopus 로고
    • note
    • We have already reported the formation of azetidines by NaH-mediated intramolecular animation of bromoallenes: see, ref. [2b].
  • 44
    • 0028150852 scopus 로고
    • To determine the intermediate of this tandem cyclization reaction, we investigated the stepwise reaction of the bromoallene 33. Treatment of the bromoallene 33 with NaH in DMF gave the pyrrolidine 37 in 86% yield. Reaction of 37 under the same reaction conditions as the one-pot reaction afforded the exo-cyclized product 34 (67%) and endo-cyclized product 35 (20%) in essentially the same product ratio. Related five-membered-ring formation by intramolecular amination of a carbon-carbon triple bond has been reported, see: a) Y. Tamaru, M. Kimura, S. Tanaka, S. Kure, Z. Yoshida, Bull. Chem. Soc. Jpn. 1994, 67, 2838-2849;
    • (1994) Bull. Chem. Soc. Jpn. , vol.67 , pp. 2838-2849
    • Tamaru, Y.1    Kimura, M.2    Tanaka, S.3    Kure, S.4    Yoshida, Z.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.