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Volumn 54, Issue 37, 2015, Pages 10903-10907

Gold(I)-Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone-Fused Polycyclic Molecules

Author keywords

alkynes; cyclizations; gold; polycycles; synthetic methods

Indexed keywords

CATALYSIS; GOLD; LINEAR TRANSFORMATIONS; MATHEMATICAL TRANSFORMATIONS; REACTION KINETICS;

EID: 84940703377     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201503599     Document Type: Article
Times cited : (40)

References (106)
  • 16
    • 84907823949 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 6294-6297;
    • (2014) Angew. Chem. , vol.126 , pp. 6294-6297
  • 19
    • 34548635326 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 3478-3519;
    • (2007) Angew. Chem. , vol.119 , pp. 3478-3519
  • 22
    • 51249100498 scopus 로고    scopus 로고
    • A. Arcadi, Chem. Rev. 2008, 108, 3266-3325;
    • (2008) Chem. Rev. , vol.108 , pp. 3266-3325
    • Arcadi, A.1
  • 27
    • 54849171800 scopus 로고    scopus 로고
    • Angew. Chem. 2008, 120, 4338-4386;
    • (2008) Angew. Chem. , vol.120 , pp. 4338-4386
  • 29
  • 31
    • 78149440697 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 5360-5369;
    • (2010) Angew. Chem. , vol.122 , pp. 5360-5369
  • 49
    • 84862681730 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 4532-4536;
    • (2012) Angew. Chem. , vol.124 , pp. 4532-4536
  • 51
    • 84872361012 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 8278-8281;
    • (2012) Angew. Chem. , vol.124 , pp. 8278-8281
  • 53
    • 84872306049 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 10785-10789;
    • (2012) Angew. Chem. , vol.124 , pp. 10785-10789
  • 55
    • 84879164599 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 2653-2659;
    • (2013) Angew. Chem. , vol.125 , pp. 2653-2659
  • 59
    • 84892373150 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 7949-7953;
    • (2013) Angew. Chem. , vol.125 , pp. 7949-7953
  • 65
    • 84927749576 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 1686-1690;
    • (2015) Angew. Chem. , vol.127 , pp. 1686-1690
  • 67
    • 84940682021 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 6971-6973.
    • (2015) Angew. Chem. , vol.127 , pp. 6971-6973
  • 68
    • 84940682022 scopus 로고    scopus 로고
    • For alternative approaches to access gold-vinylidene species, see
    • For alternative approaches to access gold-vinylidene species, see:
  • 73
    • 84930507447 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 3095-3098.
    • (2015) Angew. Chem. , vol.127 , pp. 3095-3098
  • 79
    • 33746873224 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 2232-2260;
    • (2006) Angew. Chem. , vol.118 , pp. 2232-2260
  • 85
    • 84940682023 scopus 로고    scopus 로고
    • For literature precedence of methoxide addition to metal carbene and vinylidene, see
    • For literature precedence of methoxide addition to metal carbene and vinylidene, see:
  • 88
    • 84940682024 scopus 로고    scopus 로고
    • For 2 g and 2 i, small amounts of regioisomers were isolated as a cis/trans mixture, contaminated with inseparable and unidentified side products. For 2 h, no regioisomer was detected.
    • For 2 g and 2 i, small amounts of regioisomers were isolated as a cis/trans mixture, contaminated with inseparable and unidentified side products. For 2 h, no regioisomer was detected.
  • 89
    • 84940682025 scopus 로고    scopus 로고
    • Unidentified side products were observed.
    • Unidentified side products were observed.
  • 91
    • 84940682026 scopus 로고    scopus 로고
    • Possibly, with extra stabilization, the benzylic cation is less prone to undergoing isomerization, the key step leading to the precursor for Nazarov-type cyclization.
    • Possibly, with extra stabilization, the benzylic cation is less prone to undergoing isomerization, the key step leading to the precursor for Nazarov-type cyclization.
  • 92
    • 0003102329 scopus 로고
    • For thermodynamic data of secondary and tertiary cations, see:, in (Ed.: M. T. Bowers), Academic Press, New York, .
    • For thermodynamic data of secondary and tertiary cations, see:, D. H. Aue, M. T. Bowers, in Gas Phase Ion Chemistry, Vol. 2 (Ed.:, M. T. Bowers,), Academic Press, New York, 1979, pp. 1.
    • (1979) Gas Phase Ion Chemistry, Vol. 2 , pp. 1
    • Aue, D.H.1    Bowers, M.T.2
  • 93
    • 84940682027 scopus 로고    scopus 로고
    • An alternative reaction pathway involves gold-catalyzed addition of methanol across the enediyne, which is generated upon elimination of 1 a. For related examples, see
    • An alternative reaction pathway involves gold-catalyzed addition of methanol across the enediyne, which is generated upon elimination of 1 a. For related examples, see:
  • 95
    • 0001459366 scopus 로고    scopus 로고
    • Angew. Chem. 1998, 110, 1475
    • (1998) Angew. Chem. , vol.110 , pp. 1475
  • 98
    • 84922728976 scopus 로고    scopus 로고
    • As a result, we prepared the proposed intermediate G. However, G remained intact under the standard reaction conditions in the presence of 1 equivalent of methanol. If pure methanol was used as solvent, only partial decomposition was observed.
    • R. M. P. Veenboer, S. Dupuy, S. P. Nolan, ACS Catal. 2015, 5, 1330-1334; As a result, we prepared the proposed intermediate G. However, G remained intact under the standard reaction conditions in the presence of 1 equivalent of methanol. If pure methanol was used as solvent, only partial decomposition was observed.
    • (2015) ACS Catal. , vol.5 , pp. 1330-1334
    • Veenboer, R.M.P.1    Dupuy, S.2    Nolan, S.P.3
  • 99
    • 84940682028 scopus 로고    scopus 로고
    • Only about 75 % of deuterium incorporation at the benzylic carbon atom with about 25 % of hydrogen incorporation implies that the proposed cation isomerization(C to D, Scheme 2) involves an intramolecular proton-transfer process.
    • Only about 75 % of deuterium incorporation at the benzylic carbon atom with about 25 % of hydrogen incorporation implies that the proposed cation isomerization(C to D, Scheme 2) involves an intramolecular proton-transfer process.
  • 101
  • 105
    • 0034246704 scopus 로고    scopus 로고
    • L. Yet, Chem. Rev. 2000, 100, 2963-3008;
    • (2000) Chem. Rev. , vol.100 , pp. 2963-3008
    • Yet, L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.