메뉴 건너뛰기




Volumn 51, Issue 1, 2012, Pages 183-186

Regio- and stereoselective synthesis of cyclopentenones: Intermolecular Pseudo-Pauson-Khand cyclization

Author keywords

carbenes; chromium; cyclization; enantioselectivity; tungsten

Indexed keywords

CARBENES; CYCLOPENTENONES; ELECTROPHILES; ENANTIOPURE PRODUCTS; PAUSON-KHAND REACTIONS; QUATERNARY STEREOCENTERS; STEREOSELECTIVE SYNTHESIS; TERMINAL ALKYNE;

EID: 84855278449     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105362     Document Type: Article
Times cited : (24)

References (45)
  • 5
    • 24944492823 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 5867-5870 (4+1 cyclization)
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5867-5870
  • 7
    • 54749100732 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7068-7070 (3+2 cyclization)
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7068-7070
  • 11
    • 32244445098 scopus 로고    scopus 로고
    • L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442-1443 (gold-catalyzed cycloisomerization of enynyl esters).
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1442-1443
    • Zhang, L.1    Wang, S.2
  • 15
    • 18844403627 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3022-3037
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3022-3037
  • 24
    • 9944247495 scopus 로고    scopus 로고
    • For studies about the factors that influence the reactivity of the alkene/alkyne components, see, S. E. Gibson, S. E. Lewis, N. Mainolfi, J. Organomet. Chem. 2004, 689, 3873-3890.
    • (2004) J. Organomet. Chem. , vol.689 , pp. 3873-3890
    • Gibson, S.E.1    Lewis, S.E.2    Mainolfi, N.3
  • 27
    • 77953669392 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 4463-4466
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 4463-4466
  • 35
    • 34447305203 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5020-5023.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5020-5023
  • 38
    • 67849105019 scopus 로고    scopus 로고
    • This hypothesis is supported by the fact that indole derivatives actually undergo cyclization with metal carbenes 1 through nucleophilic addition/ring closure. See:, J. Barluenga, E. Tudela, A. Ballesteros, M. Tomás, J. Am. Chem. Soc. 2009, 131, 2096-2097
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 2096-2097
    • Barluenga, J.1    Tudela, E.2    Ballesteros, A.3    Tomás, M.4
  • 39
    • 0000152844 scopus 로고    scopus 로고
    • For the reaction of alkynyl carbene complexes with enamines, see:, R. Aumann, A. G. Meyer, R. Fröhlich, Organometallics 1996, 15, 5018-5027, and references therein.
    • (1996) Organometallics , vol.15 , pp. 5018-5027
    • Aumann, R.1    Meyer, A.G.2    Fröhlich, R.3
  • 42
    • 33644965934 scopus 로고    scopus 로고
    • Comparison of Group 6 metal carbenes led us to conclude that chromium carbenes are superior in terms of chemical yield, whereas much higher asymmetric induction was reached with tungsten carbenes. This event has been previously observed. See:, J. Barluenga, R. Bernardo de La Rúa, D. de Sáa, A. Ballesteros, M. Tomás, Angew. Chem. 2005, 117, 5061-5063
    • (2005) Angew. Chem. , vol.117 , pp. 5061-5063
    • Barluenga, J.1    Bernardo De La Rúa, R.2    De Sáa, D.3    Ballesteros, A.4    Tomás, M.5
  • 43
    • 23744463209 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4981-4983, and reference [13a].
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4981-4983
  • 45
    • 32644439884 scopus 로고    scopus 로고
    • Access to such a relevant structural moiety represents a particular challenge in organic synthesis nowadays. See:, B. M. Trost, C. Jiang, Synthesis 2006, 369-396.
    • (2006) Synthesis , pp. 369-396
    • Trost, B.M.1    Jiang, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.