메뉴 건너뛰기




Volumn 43, Issue 35, 2004, Pages 4641-4644

Enantioselective organocatalytic cyclopropanation via ammonium ylides

Author keywords

Asymmetric synthesis; Cyclopropanation; Nitrogen heterocycles; Organocatalysis; Ylides

Indexed keywords

AMMONIUM COMPOUNDS; CATALYSIS; CONFORMATIONS; INTERMETALLICS; ORGANOMETALLICS; POLYCYCLIC AROMATIC HYDROCARBONS; STEREOCHEMISTRY;

EID: 5344280509     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460234     Document Type: Article
Times cited : (267)

References (24)
  • 4
    • 0000799953 scopus 로고    scopus 로고
    • For examples of asymmetric ylide-mediated cyclopropanation reactions, see: a) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482; Angew. Chem. Int. Ed. 2001, 40, 1433; b) W.-W. Lioa, K. Li, Y. Tang, J. Am. Chem. Soc. 2003, 125, 13030;
    • (2001) Angew. Chem. , vol.113 , pp. 1482
    • Aggarwal, V.K.1    Alonso, E.2    Fang, G.3    Ferrara, M.4    Hynd, G.5    Porcelloni, M.6
  • 5
    • 0035901642 scopus 로고    scopus 로고
    • For examples of asymmetric ylide-mediated cyclopropanation reactions, see: a) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482; Angew. Chem. Int. Ed. 2001, 40, 1433; b) W.-W. Lioa, K. Li, Y. Tang, J. Am. Chem. Soc. 2003, 125, 13030;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1433
  • 6
    • 0142214626 scopus 로고    scopus 로고
    • For examples of asymmetric ylide-mediated cyclopropanation reactions, see: a) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482; Angew. Chem. Int. Ed. 2001, 40, 1433; b) W.-W. Lioa, K. Li, Y. Tang, J. Am. Chem. Soc. 2003, 125, 13030;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13030
    • Lioa, W.-W.1    Li, K.2    Tang, Y.3
  • 7
    • 0038222536 scopus 로고    scopus 로고
    • for examples of carbenoid-mediated processes, see: c) S. E. Denmark, S. P. O'Connor, S. R. Wilson, Angew. Chem. 1998, 110, 1162; Angew. Chem. Int. Ed. 1998, 37, 1149, and references therein; d) A. B. Charette, C. Molinaro, C. Brochu, J. Am. Chem. Soc. 2001, 123, 12168; e) for a review, see: H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977.
    • (1998) Angew. Chem. , vol.110 , pp. 1162
    • Denmark, S.E.1    O'Connor, S.P.2    Wilson, S.R.3
  • 8
    • 0032482059 scopus 로고    scopus 로고
    • and references therein
    • for examples of carbenoid-mediated processes, see: c) S. E. Denmark, S. P. O'Connor, S. R. Wilson, Angew. Chem. 1998, 110, 1162; Angew. Chem. Int. Ed. 1998, 37, 1149, and references therein; d) A. B. Charette, C. Molinaro, C. Brochu, J. Am. Chem. Soc. 2001, 123, 12168; e) for a review, see: H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1149
  • 9
    • 0035852090 scopus 로고    scopus 로고
    • for examples of carbenoid-mediated processes, see: c) S. E. Denmark, S. P. O'Connor, S. R. Wilson, Angew. Chem. 1998, 110, 1162; Angew. Chem. Int. Ed. 1998, 37, 1149, and references therein; d) A. B. Charette, C. Molinaro, C. Brochu, J. Am. Chem. Soc. 2001, 123, 12168; e) for a review, see: H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 12168
    • Charette, A.B.1    Molinaro, C.2    Brochu, C.3
  • 10
    • 0038222536 scopus 로고    scopus 로고
    • for examples of carbenoid-mediated processes, see: c) S. E. Denmark, S. P. O'Connor, S. R. Wilson, Angew. Chem. 1998, 110, 1162; Angew. Chem. Int. Ed. 1998, 37, 1149, and references therein; d) A. B. Charette, C. Molinaro, C. Brochu, J. Am. Chem. Soc. 2001, 123, 12168; e) for a review, see: H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977.
    • (2003) Chem. Rev. , vol.103 , pp. 977
    • Lebel, H.1    Marcoux, J.-F.2    Molinaro, C.3    Charette, A.B.4
  • 12
    • 0037450150 scopus 로고    scopus 로고
    • a) C. D. Papageorgiou, S. V. Ley, M. J. Gaunt, Angew. Chem. 2003, 115, 852; Angew. Chem. Int. Ed. 2003, 42, 828;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 828
  • 14
    • 4544374715 scopus 로고    scopus 로고
    • b) N. Bremeyer, S. C. Smith, S. V. Ley, M. J. Gaunt, Angew. Chem. 2004, 116, 2735; Angew. Chem. Int. Ed. 2004, 43, 2681.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2681
  • 17
  • 18
    • 0035886887 scopus 로고    scopus 로고
    • a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3726
  • 21
    • 0038729533 scopus 로고    scopus 로고
    • and references therein
    • c) P. Chandrakala, H. Linh, N. Vignola, B. List, Angew. Chem. 2003, 115, 2891; Angew. Chem. Int. Ed. 2003, 42, 2785, and references therein.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2785
  • 22
    • 5344230297 scopus 로고    scopus 로고
    • note
    • 4), and concentrated under reduced pressure. The residue was purified by flash column chromatography.
  • 24
    • 5344233036 scopus 로고    scopus 로고
    • note
    • The amide derivatives 1c-d give higher enantioselectivities (5-10%) than reactions with 1b, although the yields are slightly lower (10-20%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.