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Volumn 38, Issue 15, 1997, Pages 2605-2608

Stereospecific rearrangements of optically active 2-aryl-3-ethenyloxiranes to give optically active β-ethenylbenzeneethanols: Benzyl vs. allyl cations and an efficient synthesis of (s)-ibuprofen

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; IBUPROFEN;

EID: 0030943449     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00425-5     Document Type: Article
Times cited : (31)

References (28)
  • 2
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    • American Chemical Society Arthur C. Cope Scholar, 1995
    • American Chemical Society Arthur C. Cope Scholar, 1995.
  • 3
    • 0342652797 scopus 로고    scopus 로고
    • NIH Chemistry-Biology Interface Trainee, UCLA, 1994-6
    • NIH Chemistry-Biology Interface Trainee, UCLA, 1994-6.
  • 11
    • 0028789552 scopus 로고
    • b) Hamon, D. P. G.; Massy-Westropp, R. A.; Newton, J. L. Tetrahedron 1995, 57, 12645; Tetrahedron Asym. 1991, 2, 1435.
    • (1991) Tetrahedron Asym. , vol.2 , pp. 1435
  • 15
    • 0001312924 scopus 로고
    • Acid catalyzed rearrangements of epoxides
    • Trost, B. M., Ed.; Pergamon; Oxford, Chapter 3.3
    • Rickborn, B. "Acid Catalyzed Rearrangements of Epoxides" in Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon; Oxford, 1991; Vol. 3, Chapter 3.3, pp. 733-775.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 733-775
    • Rickborn, B.1
  • 19
    • 0343522970 scopus 로고
    • In the absence of triethylsilane, the corresponding aldehyde was formed in 90% isolated yield. For an earlier report of a similar rearrangement at 250-280°C, see: Deux, Y. Compt. Rend. 1938, 206, 1017.
    • (1938) Compt. Rend. , vol.206 , pp. 1017
    • Deux, Y.1
  • 21
    • 0343087004 scopus 로고    scopus 로고
    • Other than a small amount of the corresponding triethylsilyl ether of 14, no significant amounts of any byproducts were isolated from this reaction
    • Other than a small amount of the corresponding triethylsilyl ether of 14, no significant amounts of any byproducts were isolated from this reaction.
  • 24
    • 0343086999 scopus 로고    scopus 로고
    • note
    • When the silane was omitted, a mixture of E and Z stereoisomers of the conjugated aldehyde, α-ethylidene-benzeneacetaldehyde, was produced so that no information concerning the sense of the rearrangement could be inferred.
  • 25
    • 0343087002 scopus 로고    scopus 로고
    • note
    • The absolute stereochemistry of 17 was assigned by analogy to the rearrangement of 3 (R = Bn) to give 4 (R = Bn).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.