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Volumn 74, Issue 15, 2009, Pages 5622-5625

A synthetic strategy for polyfunctionalized bicyclo[3.3.1]nonanes based on a tandem three-component [3 + 2] cycloaddition of α-cinnamoyl ketene-S,S-acetals with oxalyl chloride

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIASTEREO-SELECTIVITY; FUNCTIONALIZED; HIGH YIELD; OXALYL CHLORIDE; SYNTHETIC STRATEGIES; THREE COMPONENT REACTIONS; THREE-COMPONENT;

EID: 68049096177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900764s     Document Type: Article
Times cited : (22)

References (49)
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  • 11
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    • For selected examples, see: [5C + 1C] annulations and related reactions: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578-4579.
    • For selected examples, see: [5C + 1C] annulations and related reactions: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578-4579.
  • 14
    • 29944435631 scopus 로고    scopus 로고
    • For selected examples, see: [5C + 1N] annulations: (a) Dong, D.; Bi, X.; Liu, Q.; Cong, F. Chem. Commun. 2005, 3580-3582.
    • For selected examples, see: [5C + 1N] annulations: (a) Dong, D.; Bi, X.; Liu, Q.; Cong, F. Chem. Commun. 2005, 3580-3582.
  • 17
    • 29944434374 scopus 로고    scopus 로고
    • [5C + 1S] annulations: (d) Bi, X.; Dong, D.; Li, Y.; Liu, Q. J. Org. Chem. 2005, 70, 10886-10889.
    • [5C + 1S] annulations: (d) Bi, X.; Dong, D.; Li, Y.; Liu, Q. J. Org. Chem. 2005, 70, 10886-10889.
  • 19
    • 33846471698 scopus 로고    scopus 로고
    • For a review on the synthesis of butenolides by one-pot cyclization reactions of silyl enol ethers with oxalyl chloride, see: Langer, P. Synlett 2006, 3369-3381
    • For a review on the synthesis of butenolides by one-pot cyclization reactions of silyl enol ethers with oxalyl chloride, see: Langer, P. Synlett 2006, 3369-3381.
  • 21
    • 58549087741 scopus 로고    scopus 로고
    • For C-C bond-forming reactions at the α-position of functionalized ketene-S,S-acetals with aldehydes, ketones, or unsaturated ketones, see: (a) Yuan, H.-J.; Wang, M.; Liu, Y.-J.; Liu, Q. Adv. Synth. Catal. 2009, 351, 112-116.
    • For C-C bond-forming reactions at the α-position of functionalized ketene-S,S-acetals with aldehydes, ketones, or unsaturated ketones, see: (a) Yuan, H.-J.; Wang, M.; Liu, Y.-J.; Liu, Q. Adv. Synth. Catal. 2009, 351, 112-116.
  • 25
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    • 2 = 0.1419. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC-722177). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK (fax +44 1223 336033 or e-mail deposit@ccdc.cam.ac.uk).
    • 2 = 0.1419. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC-722177). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK (fax +44 1223 336033 or e-mail deposit@ccdc.cam.ac.uk).
  • 30
    • 0001603722 scopus 로고    scopus 로고
    • In general, bicyclic [3.3.1] and [3.2.1] frameworks are accomplished by reaction of appropriate C3-synthons with cyclic ketones (α,α′- annulation) or, to a lesser extent, with their enamine derivatives (β,β′-annulation). Designing efficient, short routes for the construction of polycyclic molecules is currently one of the main challenges in synthetic organic chemistry. For synthesis and synthetic application of bicyclo[3.3.1]nonanes, see: (a) Peters, J. A. Synthesis 1979, 321-336.
    • In general, bicyclic [3.3.1] and [3.2.1] frameworks are accomplished by reaction of appropriate C3-synthons with cyclic ketones (α,α′- annulation) or, to a lesser extent, with their enamine derivatives (β,β′-annulation). Designing efficient, short routes for the construction of polycyclic molecules is currently one of the main challenges in synthetic organic chemistry. For synthesis and synthetic application of bicyclo[3.3.1]nonanes, see: (a) Peters, J. A. Synthesis 1979, 321-336.
  • 31
    • 0035207263 scopus 로고    scopus 로고
    • (b) Butkus, E. Synlett 2001, 1827-1835.
    • (2001) Synlett , pp. 1827-1835
    • Butkus, E.1
  • 45
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    • For a report for the total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block, see: Snyder, S. A, Breazzano, S. P, Ross, A, G, Lin, Y, Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753-1765
    • For a report for the total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block, see: Snyder, S. A.; Breazzano, S. P.; Ross, A, G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753-1765.
  • 49
    • 68049089310 scopus 로고    scopus 로고
    • 2 = 0.3049. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC-722176). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK (fax +44 1223 336033 or e-mail deposit@ccdc.cam.ac.uk).
    • 2 = 0.3049. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC-722176). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK (fax +44 1223 336033 or e-mail deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.