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Volumn 72, Issue 5, 2007, Pages 1822-1825

Convenient access to functionalized vinylcyclopentenols from alkynyloxiranes

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLOXIRANES; HOMOPROPARGYLIC HOMOALLYLIC ALCOHOLS; METATHESIS; VINYLCYCLOPENTENOLS;

EID: 33847636651     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062107w     Document Type: Article
Times cited : (24)

References (41)
  • 1
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    • For reviews, see: a
    • For reviews, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
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    • Diver, S.T.1    Giessert, A.J.2
  • 8
    • 0034680552 scopus 로고    scopus 로고
    • Racemic allylation and crotylation: Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079.
    • (a) Racemic allylation and crotylation: Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079.
  • 9
    • 0006170068 scopus 로고    scopus 로고
    • Enantioselective allylation: Lautens, M.; Maddess, M. L.; Sauer, E. L. O.; Quellet, S. G. Org. Lett. 2002, 4, 83.
    • (b) Enantioselective allylation: Lautens, M.; Maddess, M. L.; Sauer, E. L. O.; Quellet, S. G. Org. Lett. 2002, 4, 83.
  • 10
    • 23944511120 scopus 로고    scopus 로고
    • Racemic and enantioselective propargylation: Maddess, M. L.; Lautens, M. Org. Lett. 2005, 7, 3557.
    • (c) Racemic and enantioselective propargylation: Maddess, M. L.; Lautens, M. Org. Lett. 2005, 7, 3557.
  • 11
    • 0034696984 scopus 로고    scopus 로고
    • For additional examples, see: a
    • For additional examples, see: (a) Hertweck, C.; Boland, W. J. Org. Chem. 2000, 65, 2458.
    • (2000) J. Org. Chem , vol.65 , pp. 2458
    • Hertweck, C.1    Boland, W.2
  • 16
    • 0000048258 scopus 로고
    • Trost, B. M, Flemming, T, Eds, Pergamon: Oxford
    • (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, T., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 315.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 315
    • Oppolzer, W.1
  • 26
    • 1642284120 scopus 로고    scopus 로고
    • For typical applications, see: (b) Pauson-Khand reaction: Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominquez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32.
    • For typical applications, see: (b) Pauson-Khand reaction: Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominquez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32.
  • 27
    • 12744278006 scopus 로고    scopus 로고
    • [4 + 2 + 2] cycloadditions: Evans, P. A.; Baum, E. W.; Fazal, A. N.; Pink, M. Chem, Commun. 2005, 63 and references cited therein.
    • (c) [4 + 2 + 2] cycloadditions: Evans, P. A.; Baum, E. W.; Fazal, A. N.; Pink, M. Chem, Commun. 2005, 63 and references cited therein.
  • 29
    • 33847675547 scopus 로고    scopus 로고
    • Details are provided in the Supporting Information
    • Details are provided in the Supporting Information.
  • 30
    • 0033522938 scopus 로고    scopus 로고
    • Potassium allyl and crotyl triflouroborates are readily prepared air- and moisture-insensitive solids; see: (a) Batey, R. A, Thadani, A. N, Smil, D. V. Tetrahedron Lett. 1999, 40, 4289
    • Potassium allyl and crotyl triflouroborates are readily prepared air- and moisture-insensitive solids; see: (a) Batey, R. A.; Thadani, A. N.; Smil, D. V. Tetrahedron Lett. 1999, 40, 4289.
  • 33
    • 33847662599 scopus 로고    scopus 로고
    • Either antiopode is readily accessible by modification of the nucleophile, ent-32 gave (R)-10 in 83% yield and 77% ee.
    • Either antiopode is readily accessible by modification of the nucleophile, ent-32 gave (R)-10 in 83% yield and 77% ee.
  • 34
    • 33845550192 scopus 로고    scopus 로고
    • The absolute configuration may be predicted from analogy with previous results. Compound 32 is known to give re face attack, while ent-32 provides the enantiomer; see: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
    • The absolute configuration may be predicted from analogy with previous results. Compound 32 is known to give re face attack, while ent-32 provides the enantiomer; see: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
  • 36
    • 1642373105 scopus 로고    scopus 로고
    • For examples of microwave-assisted metathesis reactions, see: (a) Balan, D, Adolfsson, H. Tetrahedron Lett. 2004, 45, 3089
    • For examples of microwave-assisted metathesis reactions, see: (a) Balan, D.; Adolfsson, H. Tetrahedron Lett. 2004, 45, 3089.
  • 39
    • 33847636206 scopus 로고    scopus 로고
    • Control experiments using microwave vials under thermal conditions indicated no appreciable difference in reaction yield or rate
    • Control experiments using microwave vials under thermal conditions indicated no appreciable difference in reaction yield or rate.
  • 40
    • 3042833046 scopus 로고    scopus 로고
    • For other examples of oxygen chelation effects in metathesis events, see:, and references cited therein
    • For other examples of oxygen chelation effects in metathesis events, see: Maddess, M. L.; Lautens, M. Org. Lett. 2004, 6, 1883 and references cited therein.
    • (2004) Org. Lett , vol.6 , pp. 1883
    • Maddess, M.L.1    Lautens, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.