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Volumn 133, Issue 20, 2011, Pages 7696-7699

Gold and brønsted acid catalyzed hydride shift onto allenes: Divergence in product selectivity

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SELECTIVITY; GOLD; HYDRIDES;

EID: 79957731780     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202336p     Document Type: Article
Times cited : (102)

References (42)
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    • For recent reviews on gold catalysis, see: Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208
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  • 20
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    • No example of a direct gold-catalyzed hydride transfer onto an allene has been reported. For examples of 1,5-hydride shifts observed in gold(I)-catalyzed processes, see
    • No example of a direct gold-catalyzed hydride transfer onto an allene has been reported. For examples of 1,5-hydride shifts observed in gold(I)-catalyzed processes, see: Harrak, Y.; Simonneau, A.; Malacria, M.; Gandon, V.; Fensterbank, L. Chem. Commun. 2010, 46, 865
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    • Harrak, Y.1    Simonneau, A.2    Malacria, M.3    Gandon, V.4    Fensterbank, L.5
  • 25
    • 67650311554 scopus 로고    scopus 로고
    • For examples of Lewis acid catalyzed sequences of a hydride transfer from an ether to an activated alkene followed by a cyclization, see
    • For examples of Lewis acid catalyzed sequences of a hydride transfer from an ether to an activated alkene followed by a cyclization, see: McQuaid, K. M.; Long, J. Z.; Sames, D. Org. Lett. 2009, 11, 2972
    • (2009) Org. Lett. , vol.11 , pp. 2972
    • McQuaid, K.M.1    Long, J.Z.2    Sames, D.3
  • 29
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    • 1H NMR spectroscopy
    • 1H NMR spectroscopy.
  • 30
    • 79957692107 scopus 로고    scopus 로고
    • The spiroether structural unit is found in a number of natural products
    • The spiroether structural unit is found in a number of natural products.
  • 31
    • 79957749459 scopus 로고    scopus 로고
    • The reaction could not be performed with monosubstituted allenes
    • The reaction could not be performed with monosubstituted allenes.
  • 32
    • 79957746255 scopus 로고    scopus 로고
    • (3) and the pendant alkene group in the chairlike transition state leading to intermediate 20 (see Scheme 1)
    • (3) and the pendant alkene group in the chairlike transition state leading to intermediate 20 (see Scheme 1).
  • 33
    • 79957693981 scopus 로고    scopus 로고
    • Compound 16e corresponds to an open form of the bicyclic compound generally obtained. Its formation probably results from a gold-catalyzed oxepane ring opening
    • Compound 16e corresponds to an open form of the bicyclic compound generally obtained. Its formation probably results from a gold-catalyzed oxepane ring opening.
  • 36
    • 79957715624 scopus 로고    scopus 로고
    • 1H NMR spectroscopy
    • 1H NMR spectroscopy.
  • 37
    • 79957744431 scopus 로고    scopus 로고
    • Compounds 10 and 11 remain unchanged when they were separately treated with gold catalyst 13 thus precluding the formation of 11 from 10 and 10 from 11
    • Compounds 10 and 11 remain unchanged when they were separately treated with gold catalyst 13 thus precluding the formation of 11 from 10 and 10 from 11.
  • 38
    • 79957703709 scopus 로고    scopus 로고
    • 2 catalysis, and even after prolonged reaction times, compound 10 was not transformed into compound 11 thus precluding an isomerization of 10 into 18 via 20
    • 2 catalysis, and even after prolonged reaction times, compound 10 was not transformed into compound 11 thus precluding an isomerization of 10 into 18 via 20.
  • 39
    • 79957763348 scopus 로고    scopus 로고
    • (3) in products 10(D) and 11(D) was equally shared between the two available positions. This specific pattern tends to show that no memory of chirality is involved in the hydroalkylation of allene 9. The nucleophilic trapping of oxonium 17 should proceed in this case with no facial selectivity
    • (3) in products 10(D) and 11(D) was equally shared between the two available positions. This specific pattern tends to show that no memory of chirality is involved in the hydroalkylation of allene 9. The nucleophilic trapping of oxonium 17 should proceed in this case with no facial selectivity.
  • 40
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    • For a (3,5) oxonium-ene type cyclization leading to tetrahydropyrans of types 23 and 24, see
    • For a (3,5) oxonium-ene type cyclization leading to tetrahydropyrans of types 23 and 24, see: Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669
    • (2001) Org. Lett. , vol.3 , pp. 2669
    • Loh, T.-P.1    Hu, Q.-Y.2    Tan, K.-T.3    Cheng, H.-S.4
  • 41
    • 79957669348 scopus 로고    scopus 로고
    • 1H NMR spectroscopy of the crude reaction mixture.
    • 1H NMR spectroscopy of the crude reaction mixture.
  • 42
    • 79957569118 scopus 로고    scopus 로고
    • For a recent review on gold-mediated C-H bond functionalization, see
    • For a recent review on gold-mediated C-H bond functionalization, see: Boorman, T. C.; Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 1910
    • Boorman, T.C.1    Larrosa, I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.