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Volumn 349, Issue 10, 2007, Pages 1619-1623

Gold(I)- and brønsted acid-catalyzed ring-opening of unactivated vinylcyclopropanes with sulfonamides

Author keywords

Catalysis; Gold; Hydroamination; Ring opening; Vinylcyclopropanes

Indexed keywords


EID: 34547154223     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700006     Document Type: Article
Times cited : (43)

References (44)
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    • For recent representative examples of hydroamination reactions, see, a
    • For recent representative examples of hydroamination reactions, see : a) N. Sakai, A. Ridder, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 8134;
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    • For recent reviews on hydroamination, see, a
    • For recent reviews on hydroamination, see : a) K. C. Hultzsch, Adv. Synth. Catal. 2005, 347, 367;
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    • For hydroamination reactions catalyzed by gold complexes, see: a R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555, and references cited therein;
    • For hydroamination reactions catalyzed by gold complexes, see: a) R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555, and references cited therein;
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    • A. S. K. Hashmi, M. Rudolph, S. Schymura, J. Visus, W. Frey, Eur. J. Org. Chem. 2006, 4905; for a recent review on gold catalysis, see:
    • f) A. S. K. Hashmi, M. Rudolph, S. Schymura, J. Visus, W. Frey, Eur. J. Org. Chem. 2006, 4905; for a recent review on gold catalysis, see:
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    • H. M. Senn, P. E. Blochl, A. Togni, J. Am. Chem. Soc. 2000, 122, 4098;
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    • For the synthesis of homoallylic amine derivatives, see, a
    • For the synthesis of homoallylic amine derivatives, see : a) E. C. Burger, J. A. Tunge, J. Am. Chem. Soc. 2006, 128, 10002;
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 10002
    • Burger, E.C.1    Tunge, J.A.2
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    • 1H NOESY NMR experiments: see Supporting Information.
    • 1H NOESY NMR experiments: see Supporting Information.
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    • A similar ring-opening reaction leading to homoallylic amine derivatives has been observed recently by Carreira and co-workers in the Co- or Mn-catalyzed radical hydrohydrazination of vinylcyclopropanes. However, there is no experimental evidence that the Au-catalyzed reaction takes place via radical intermediates; see: J. Waser, B. Gaspar, H. Nambu, E. M. Carreira, J. Am. Chem. Soc. 2006, 128, 11693
    • A similar ring-opening reaction leading to homoallylic amine derivatives has been observed recently by Carreira and co-workers in the Co- or Mn-catalyzed radical hydrohydrazination of vinylcyclopropanes. However, there is no experimental evidence that the Au-catalyzed reaction takes place via radical intermediates; see: J. Waser, B. Gaspar, H. Nambu, E. M. Carreira, J. Am. Chem. Soc. 2006, 128, 11693.
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    • Crystallographic data (excluding structure factors) for the structure of compound 2ab have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-622306. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) + 44 1223/336-033; e-mail: deposit@ccdc.cam.ac.uk].
    • Crystallographic data (excluding structure factors) for the structure of compound 2ab have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-622306. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) + 44 1223/336-033; e-mail: deposit@ccdc.cam.ac.uk].
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    • Very recently, Shi et al. reported the synthesis of pyrrolidines via an Au-catalyzed domino ring-opening/ring-closing reaction of methylene- cyclopropanes with sulfonamides, in which compounds of type 2 occur as intermediates; see: M. Shi, L.-P. Liu, J. Tang, Org. Lett. 2006, 8, 4043.
    • Very recently, Shi et al. reported the synthesis of pyrrolidines via an Au-catalyzed domino ring-opening/ring-closing reaction of methylene- cyclopropanes with sulfonamides, in which compounds of type 2 occur as intermediates; see: M. Shi, L.-P. Liu, J. Tang, Org. Lett. 2006, 8, 4043.
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    • For similar observations, see
    • For similar observations, see: Y. Chen, M. Shi, J. Org. Chem. 2004, 69, 426.
    • (2004) J. Org. Chem , vol.69 , pp. 426
    • Chen, Y.1    Shi, M.2
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    • For very recent N-H and O-H addition to simple olefins catalyzed by Brønsted acids, see : a Zi. Li, J. Zhang, C. Brouwer, C.-G. Yang, N. W. Reich, C. He, Org. Lett. 2006, 8, 4175;
    • For very recent N-H and O-H addition to simple olefins catalyzed by Brønsted acids, see : a) Zi. Li, J. Zhang, C. Brouwer, C.-G. Yang, N. W. Reich, C. He, Org. Lett. 2006, 8, 4175;
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    • For previous reports discussing gold versus Brønsted catalysis, see: a G. Dyker, E. Muth, A. S. K. Hashmi, L. Ding, Adv. Synth. Catal. 2003, 345, 1247;
    • For previous reports discussing gold versus Brønsted catalysis, see: a) G. Dyker, E. Muth, A. S. K. Hashmi, L. Ding, Adv. Synth. Catal. 2003, 345, 1247;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.