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Volumn 46, Issue 13, 2007, Pages 2310-2313

Catalyzed tandem reaction of 3-silyloxy-1,5-enynes consisting of cyclization and pinacol rearrangement

Author keywords

Cyclization; Domino reactions; Gold; Homogeneous catalysis; Rearrangement

Indexed keywords

ALCOHOLS; CATALYSTS; CHEMICAL REACTIONS; CYCLIZATION; GOLD; HOMOGENIZATION METHOD; SILVER;

EID: 34250333483     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604544     Document Type: Article
Times cited : (141)

References (75)
  • 2
    • 0035817978 scopus 로고    scopus 로고
    • For additional examples, see: a
    • For additional examples, see: a) J.-H. Youn, J. Lee, J. K. Cha, Org. Lett. 2001, 3, 2935;
    • (2001) Org. Lett , vol.3 , pp. 2935
    • Youn, J.-H.1    Lee, J.2    Cha, J.K.3
  • 5
    • 33750977591 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7134;
    • (2006) Chem. Int. Ed , vol.45 , pp. 7134
    • Angew1
  • 11
    • 33748529350 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5878;
    • (2006) Chem. Int. Ed , vol.45 , pp. 5878
    • Angew1
  • 13
    • 33748637774 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5452;
    • (2006) Chem. Int. Ed , vol.45 , pp. 5452
    • Angew1
  • 18
    • 18744401616 scopus 로고    scopus 로고
    • For catalytic cycloisomerizations of 1,5-enynes with a concomitant nucleophilic trapping, see: a
    • For catalytic cycloisomerizations of 1,5-enynes with a concomitant nucleophilic trapping, see: a) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2005, 127, 6962;
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 6962
    • Zhang, L.1    Kozmin, S.A.2
  • 20
    • 33750686291 scopus 로고    scopus 로고
    • For further work in 1,5-enyne cycloisomerizations involving π activation, see: a
    • For further work in 1,5-enyne cycloisomerizations involving π activation, see: a) S. Wang, L. Zhang, J. Am. Chem. Soc. 2006, 128, 14274;
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 14274
    • Wang, S.1    Zhang, L.2
  • 23
  • 25
    • 33746305520 scopus 로고    scopus 로고
    • Reviews on transition-metal-catalyzed reactions of enynes: a
    • Reviews on transition-metal-catalyzed reactions of enynes: a) S. Ma, S. Yu, Z. Gu, Angew. Chem. 2006, 118, 206;
    • (2006) Angew. Chem , vol.118 , pp. 206
    • Ma, S.1    Yu, S.2    Gu, Z.3
  • 26
  • 28
    • 18044386806 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2328;
    • (2005) Chem. Int. Ed , vol.44 , pp. 2328
    • Angew1
  • 31
    • 34250883045 scopus 로고    scopus 로고
    • For selected examples on sequences proceeding by π activation with concomitant nucleophilic trapping, see, for example: Alkynes: a P. Y. Toullec, E. Genin, L. Leseurre, J.-P. Genêt, V. Michelet, Angew. Chem. 2006, 118, 7587;
    • For selected examples on sequences proceeding by π activation with concomitant nucleophilic trapping, see, for example: Alkynes: a) P. Y. Toullec, E. Genin, L. Leseurre, J.-P. Genêt, V. Michelet, Angew. Chem. 2006, 118, 7587;
  • 32
    • 33751200973 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7427;
    • (2006) Chem. Int. Ed , vol.45 , pp. 7427
    • Angew1
  • 34
    • 33745661090 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 2091;
    • (2006) Chem. Int. Ed , vol.45 , pp. 2091
    • Angew1
  • 40
  • 43
  • 44
    • 33646576245 scopus 로고    scopus 로고
    • Alkenes: j A. Fürstner, C. Aïssa, J. Am. Chem. Soc. 2006, 128, 6306;
    • Alkenes: j) A. Fürstner, C. Aïssa, J. Am. Chem. Soc. 2006, 128, 6306;
  • 46
  • 49
    • 33845546747 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7896;
    • (2006) Chem. Int. Ed , vol.45 , pp. 7896
    • Angew1
  • 51
    • 27744595601 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6990;
    • (2005) Chem. Int. Ed , vol.44 , pp. 6990
    • Angew1
  • 53
    • 33748774422 scopus 로고    scopus 로고
    • For recent examples of Au-catalyzed domino processes, see: a
    • For recent examples of Au-catalyzed domino processes, see: a) P. Dubé, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 12062;
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 12062
    • Dubé, P.1    Toste, F.D.2
  • 59
    • 33750156253 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6704;
    • (2006) Chem. Int. Ed , vol.45 , pp. 6704
    • Angew1
  • 63
    • 33748787678 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5991.
    • (2006) Chem. Int. Ed , vol.45 , pp. 5991
    • Angew1
  • 64
    • 34250812830 scopus 로고    scopus 로고
    • Addition of tBuOH (1.1 equiv) provided 2a in 86% yield, while the use of MeOH produced a mixture of unidentified compounds.
    • Addition of tBuOH (1.1 equiv) provided 2a in 86% yield, while the use of MeOH produced a mixture of unidentified compounds.
  • 65
    • 34250880490 scopus 로고    scopus 로고
    • The rearrangement of 1,5-enyne precursors was strictly limited to substrates that contain alkenes bearing an additional substituent at C2. Attempted rearrangement of 1,2-disubstituted alkenes afforded at most trace amounts of the desired cyclopentene under the reaction conditions. In these cases, the formation of the major product can be rationalized by a sequence consisting of elimination and subsequent hydration of the triple bond.
    • The rearrangement of 1,5-enyne precursors was strictly limited to substrates that contain alkenes bearing an additional substituent at C2. Attempted rearrangement of 1,2-disubstituted alkenes afforded at most trace amounts of the desired cyclopentene under the reaction conditions. In these cases, the formation of the major product can be rationalized by a sequence consisting of elimination and subsequent hydration of the triple bond.
  • 66
    • 34250884286 scopus 로고    scopus 로고
    • 1H NMR analysis of crude reaction mixtures.
    • 1H NMR analysis of crude reaction mixtures.
  • 70
    • 34250865328 scopus 로고    scopus 로고
    • I, see: N. Morita, N. Krause, Angew. Chem. 2006, 118, 1930;
    • I, see: N. Morita, N. Krause, Angew. Chem. 2006, 118, 1930;
  • 71
    • 33745652988 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1897, and references therein.
    • Angew. Chem. Int. Ed. 2006, 45, 1897, and references therein.
  • 72
    • 24944453027 scopus 로고    scopus 로고
    • 3CN, 11 %]: T. Yao, X. Zhang, R. C. Larock, J. Org. Chem. 2005, 70, 7679, and references herein.
    • 3CN, 11 %]: T. Yao, X. Zhang, R. C. Larock, J. Org. Chem. 2005, 70, 7679, and references herein.
  • 73
    • 32644446865 scopus 로고    scopus 로고
    • For examples of trapping vinylgold species by electrophilic iodine, see: a A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515;
    • For examples of trapping vinylgold species by electrophilic iodine, see: a) A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.