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Volumn 52, Issue 29, 2011, Pages 3714-3717

Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane

Author keywords

Ambiphilic alkenes; C H acids; Stereoselective alkene synthesis; Trifluoromethyl sulfones (triflones); Trimethylsilyldiazomethane

Indexed keywords

ALKENE; CARBONYL DERIVATIVE; DIAZOMETHANE; TRIMETHYLSILYLDIAZOMETHANE; UNCLASSIFIED DRUG;

EID: 79959280058     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.015     Document Type: Article
Times cited : (15)

References (23)
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    • For a related example of O-methylation of acetone dicarboxylic acid anhydride, see
    • For a related example of O-methylation of acetone dicarboxylic acid anhydride, see: Ray, J. A.; Harris, T. M. Tetrahedron Lett. 1982, 23, 1971.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 1971
    • Ray, J.A.1    Harris, T.M.2
  • 9
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    • note
    • Sodium trifluoromethanesulfinate was purchased from TCI America and used as received.
  • 10
    • 79959213193 scopus 로고    scopus 로고
    • note
    • Trimethylsilyldiazomethane was purchased from Aldrich Chemical Corp. as a 2 M solution in diethyl ether and used as received.
  • 11
    • 79959210493 scopus 로고    scopus 로고
    • note
    • E/Z stereochemistry of 3 was not assigned but the isomer ratio was found to be 1.8:1.
  • 15
    • 33947456919 scopus 로고
    • For a related preparation of ketone 22, see
    • For a related preparation of ketone 22, see: Wagner, R. B.; Moore, J. A. J. Am. Chem. Soc. 1950, 72, 2884.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 2884
    • Wagner, R.B.1    Moore, J.A.2
  • 16
    • 0001770782 scopus 로고
    • For two examples of cyclic a-perhalosulfonyl ketones exhibiting keto-enol tautomerism, see
    • For two examples of cyclic a-perhalosulfonyl ketones exhibiting keto-enol tautomerism, see: (a) Kobayashi, Y.; Yoshida, T.; Kumadaki, I. Tetrahedron Lett. 1979, 3865;
    • (1979) Tetrahedron Lett. , pp. 3865
    • Kobayashi, Y.1    Yoshida, T.2    Kumadaki, I.3
  • 19
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    • Trimethylsilyldiazomethane
    • Wiley-InterScience, Posted September 15, accessed March 2, 2011
    • Trimethylsilyldiazomethane. e-Encyclopedia of Reagents for Organic Synthesis [Online]; Wiley-InterScience, Posted September 15, 2006. http://www.mrw.interscience.wiley.com/eros/articles/rt298/frame.html (accessed March 2, 2011).
    • (2006) e-Encyclopedia of Reagents for Organic Synthesis [Online]
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    • note
    • See Supplementary data for full experimental details.
  • 22
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    • For recent reviews on donor-acceptor cyclopropanes, see
    • For recent reviews on donor-acceptor cyclopropanes, see: (a) Lebold, T. P.; Kerr, M. A. Pure App. Chem. 2010, 82, 1797;
    • (2010) Pure App. Chem. , vol.82 , pp. 1797
    • Lebold, T.P.1    Kerr, M.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.