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Volumn 130, Issue 6, 2008, Pages 1814-1815

Au-containing all-carbon 1,4-dipoles: Generation and [4 + 2] annulation in the formation of carbo-/heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 BENZENESULFONYLETHYL) 1H INDOLE; CARBOCYCLIC COMPOUND; CARBON; CYCLOPROPANE DERIVATIVE; GOLD; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 39049105773     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077948e     Document Type: Article
Times cited : (206)

References (32)
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    • For a review on [4 + 2] benzannulation, see: (g) Patil, N. T.; Yamamoto, Y. Arkivoc 2007, (v), 6-19.
    • For a review on [4 + 2] benzannulation, see: (g) Patil, N. T.; Yamamoto, Y. Arkivoc 2007, (v), 6-19.
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    • For reviews on all-carbon 1,3-dipoles and their surrogates, see: a
    • For reviews on all-carbon 1,3-dipoles and their surrogates, see: (a) Yamago, S.; Nakamura, E. Org. React. 2002, 61, 1-217.
    • (2002) Org. React , vol.61 , pp. 1-217
    • Yamago, S.1    Nakamura, E.2
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    • 1st ed, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford; New York
    • (b) Little, R. D. Comprehensive Organic Synthesis, 1st ed.; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford; New York, 1991; Vol. 3, pp 239-270.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 239-270
    • Little, R.D.1
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    • 1st ed, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford; New York
    • (c) Chan, D. M. T. Comprehensive Organic Synthesis, 1st ed.; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford; New York, 1991; Vol. 3, pp 271-314.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 271-314
    • Chan, D.M.T.1
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    • For our recent studies evoking all-carbon 1,3-dipoles, see: d
    • For our recent studies evoking all-carbon 1,3-dipoles, see: (d) Huang, X.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 6398-6399.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 6398-6399
    • Huang, X.1    Zhang, L.2
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    • For examples of surrogates of all carbon 1,4-dipoles, see: (a) Zhu, X.-F, Lan, J, Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716-4717
    • For examples of surrogates of all carbon 1,4-dipoles, see: (a) Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716-4717.
  • 20
    • 33750686291 scopus 로고    scopus 로고
    • We have previously reported a study involving the generation and cyclization of Au-containing all-carbon 1,6-dipoles, see: Wang, S, Zhang, L. J. Am. Chem. Soc. 2006, 128, 14274-14275
    • We have previously reported a study involving the generation and cyclization of Au-containing all-carbon 1,6-dipoles, see: Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 14274-14275.
  • 21
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    • The reaction between an electrophile and an alkenylgold is most likely involving the attack of the electrophile by the alkene π-electrons accompanied by simultaneous Au-C bond cleavage. For selected examples, see: (a) Shi, Z, He, C. J. Am. Chem. Soc. 2004, 126, 5964-5965
    • The reaction between an electrophile and an alkenylgold is most likely involving the attack of the electrophile by the alkene π-electrons accompanied by simultaneous Au-C bond cleavage. For selected examples, see: (a) Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964-5965.
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    • Reference 5
    • (c) Reference 5.
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    • For the first study of Au-catalyzed cyclization of propargylic ketones, see
    • For the first study of Au-catalyzed cyclization of propargylic ketones, see: Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 2285-2288
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  • 27
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    • The use of the polar 2-benzenesulfonylethyl group to protect indole is to facilitate product purification
    • The use of the polar 2-benzenesulfonylethyl group to protect indole is to facilitate product purification.
  • 30
    • 39049113258 scopus 로고    scopus 로고
    • The expected cis ring fusion of 3 was supported by 1D NOESY.
    • The expected cis ring fusion of 3 was supported by 1D NOESY.
  • 31
    • 39049165056 scopus 로고    scopus 로고
    • These substituted ketones 4 were prepared diastereomerically pure; see the Supporting Information for details.
    • These substituted ketones 4 were prepared diastereomerically pure; see the Supporting Information for details.
  • 32
    • 39049104993 scopus 로고    scopus 로고
    • The diastereomers were not separable. In the case of 5c, 1D NOESY studies indicated that the isomer with the Me group residing on the concave side of the tetracycle was the major one.
    • The diastereomers were not separable. In the case of 5c, 1D NOESY studies indicated that the isomer with the Me group residing on the concave side of the tetracycle was the major one.


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