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Volumn 52, Issue 50, 2011, Pages 6763-6766

Desymmetrization of meso [3.2.1]oxabicyclic systems using metal-catalysed asymmetric intramolecular C-H insertion

Author keywords

C H insertion; Carbene; Desymmetrization; Diazo compounds; Oxabicyclic compounds

Indexed keywords

COPPER; KETONE DERIVATIVE; MESO 8 OXABICYCLO( 3.2.1 )OCTEN 3 ONE; OCTANE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 80755175788     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.026     Document Type: Article
Times cited : (8)

References (57)
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    • For recent reviews on the reactions of α-diazocarbonyl compounds, see: Y. Zhang, and J. Wang Chem. Commun. 2009 5350 5361
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    • Zhang, Y.1    Wang, J.2
  • 31
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    • The ketoester intermediates were not isolated, but were subjected to Krapcho decarboxylation to yield 3a or 3b in one-pot
    • The ketoester intermediates were not isolated, but were subjected to Krapcho decarboxylation to yield 3a or 3b in one-pot.
  • 34
    • 80755187427 scopus 로고    scopus 로고
    • note
    • The syntheses of substrates 2b-d are similar to the synthesis of 2a reported previously, see Ref. 14 Detailed experimental procedures can be found in the Supplementary data of this Letter.
  • 44
    • 0029022070 scopus 로고
    • For a review on metal carbene-mediated O-H insertion, see
    • For a review on metal carbene-mediated O-H insertion, see: D.J. Miller, and C.J. Moody Tetrahedron 51 1995 10811 10843
    • (1995) Tetrahedron , vol.51 , pp. 10811-10843
    • Miller, D.J.1    Moody, C.J.2
  • 45
    • 80755187428 scopus 로고    scopus 로고
    • note
    • These results are not due to our inability to exclude moisture rigorously under the reaction conditions. Using other substrates with a similar handling and reaction set-up, vide infra, carbene formation and insertion occurred in high yields.
  • 54
    • 80755173623 scopus 로고    scopus 로고
    • note
    • 2 has been used in the preparation of the complex, Cu(II) is reduced to Cu(I) in the presence of diazo compounds, which is the generally accepted reactive species.
  • 55
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    • A methine C-H bond is more reactive than a methylene C-H bond towards metal carbene-mediated C-H bond insertion, see
    • A methine C-H bond is more reactive than a methylene C-H bond towards metal carbene-mediated C-H bond insertion, see: D.F. Taber, and R.E. Ruckle J. Am. Chem. Soc. 108 1986 7686 7693
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7686-7693
    • Taber, D.F.1    Ruckle, R.E.2
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    • For examples of carbene insertion into the α position of a silyl group, see: M. Hrytsak, and T. Durst Heterocycles 26 1987 2393 2409
    • (1987) Heterocycles , vol.26 , pp. 2393-2409
    • Hrytsak, M.1    Durst, T.2
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    • note
    • +): 296.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.