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Volumn 132, Issue 14, 2010, Pages 5018-5020

A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-CANCER AGENTS; CONJUGATED ALKENES; E-ISOMERS; MILD REACTION CONDITIONS; OLEFINATION; OLEFINATION REACTION; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; STERIC PROPERTIES; SULFONYL GROUPS; WITTIG REACTION;

EID: 77950811184     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910238f     Document Type: Article
Times cited : (150)

References (44)
  • 1
    • 77950836666 scopus 로고    scopus 로고
    • Wiley-VCH, Weinheim, Germany,. Preparation of Alkenes: A Practical Approach; Oxford University Press: Oxford, UK, 1996. In Comprehensive Organic Synthesis;, Eds.; Pergamon: Oxford, UK, 1991
    • Takeda, T. Modern Carbonyl Olefination; Wiley-VCH, Weinheim, Germany, 2004. Williams, J. M. J. Preparation of Alkenes: A Practical Approach; Oxford University Press: Oxford, UK, 1996. Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M. and Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 1, p 729.
    • (2004) Modern Carbonyl Olefination , vol.1 , pp. 729
    • Takeda, T.1    Williams, J.M.J.2    Kelly, S.E.3    Trost, B.M.4    Fleming, I.5
  • 4
    • 77950793649 scopus 로고    scopus 로고
    • Hu, Y.-F. and Lin, G.-Q., Eds.; Chemical Industry Press: Beijing, China
    • Ju, Y. In Modern Organic Reactions (in Chinese) Hu, Y.-F. and Lin, G.-Q., Eds.; Chemical Industry Press: Beijing, China, 2008; Vol. 3, p 413.
    • (2008) Modern Organic Reactions (In Chinese) , vol.3 , pp. 413
    • Ju, Y.1
  • 26
    • 77950841449 scopus 로고    scopus 로고
    • A stepwise process involving initial carbon-carbon bond formation leading to a betaine intermediate was proposed for the formal [2+2] cycloaddition. Alternatively, the 1,2-azaphosphetane intermediate can be generated directly through a four-center transition state analogous to that suggested for the Wittig reaction (see refs 2b, 2c, and 3)
    • A stepwise process involving initial carbon-carbon bond formation leading to a betaine intermediate was proposed for the formal [2+2] cycloaddition. Alternatively, the 1,2-azaphosphetane intermediate can be generated directly through a four-center transition state analogous to that suggested for the Wittig reaction (see refs 2b, 2c, and 3).
  • 31
    • 77950818411 scopus 로고    scopus 로고
    • The reaction was quenched with water upon completion, and byproduct iminophosphorane was decomposed by water to give triphenylphosphine oxide and a primary sulfonamide
    • The reaction was quenched with water upon completion, and byproduct iminophosphorane was decomposed by water to give triphenylphosphine oxide and a primary sulfonamide.
  • 32
    • 11244253797 scopus 로고    scopus 로고
    • 1H NMR analysis within 3 days owing to the isomerization of (Z)-alkenes under the influence of light and air at room temperature. For a relevant study, see
    • 1H NMR analysis within 3 days owing to the isomerization of (Z)-alkenes under the influence of light and air at room temperature. For a relevant study, see: Ren, Y., Che, Y., Ma, W., Zhang, X., Shen, T., and Zhao, J. New J. Chem. 2004, 28, 1464
    • (2004) New J. Chem. , vol.28 , pp. 1464
    • Ren, Y.1    Che, Y.2    Ma, W.3    Zhang, X.4    Shen, T.5    Zhao, J.6
  • 33
    • 77950837367 scopus 로고    scopus 로고
    • 1 group, and Ar group contribute to the stereoselectivity for the formation of the 1,2-azaphosphetane intermediate leading to an alkene product. Since the electronic and steric properties of an aryl group, alkenyl group, and alkyl group are significantly different from each other, it is plausible that each type of imine shown in Table 2 needs a different N -sulfonyl group to control the stereoselectivity synergically in its olefination reaction with a benzylidenetriphenylphosphorane
    • 1 group, and Ar group contribute to the stereoselectivity for the formation of the 1,2-azaphosphetane intermediate leading to an alkene product. Since the electronic and steric properties of an aryl group, alkenyl group, and alkyl group are significantly different from each other, it is plausible that each type of imine shown in Table 2 needs a different N -sulfonyl group to control the stereoselectivity synergically in its olefination reaction with a benzylidenetriphenylphosphorane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.