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Volumn 72, Issue 17, 2007, Pages 6614-6617

Highly stereoselective epoxidation of α-methyl-γ-hydroxy- α,β-unsaturated esters: Rationalization and synthetic applications

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDATION; GAMMA RAYS; ISOMERS; MATHEMATICAL MODELS; STEREOSELECTIVITY; SUBSTITUTION REACTIONS;

EID: 34547951510     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0709955     Document Type: Article
Times cited : (34)

References (26)
  • 10
    • 0001562620 scopus 로고    scopus 로고
    • Similar selectivities have been repotted in the conjugate addition of amides to nonsubstituted and α-methyl-substituted γ-methoxyenoates: (a) Yamamoto, Y, Chounan, Y, Nishii, S, Ibuka, T, Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652-7660
    • Similar selectivities have been repotted in the conjugate addition of amides to nonsubstituted and α-methyl-substituted γ-methoxyenoates: (a) Yamamoto, Y.; Chounan, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652-7660.
  • 12
    • 34547952986 scopus 로고    scopus 로고
    • This reaction had been previously conducted by C. Benezra et al, see ref 5e repotting a mixture of sulfoxides; however, we observed only one sulfoxide although, if the reaction is conducted with an excess of oxidant, then a mixture of sulfoxide and sulfone is obtained
    • This reaction had been previously conducted by C. Benezra et al. (see ref 5e) repotting a mixture of sulfoxides; however, we observed only one sulfoxide although, if the reaction is conducted with an excess of oxidant, then a mixture of sulfoxide and sulfone is obtained.
  • 17
    • 0000332156 scopus 로고    scopus 로고
    • For other syntheses of 15 see (e) Barbier, P.; Benezra, C. J. Org. Chem. 1983, 48, 2705-2709.
    • For other syntheses of 15 see (e) Barbier, P.; Benezra, C. J. Org. Chem. 1983, 48, 2705-2709.
  • 23
    • 34547932591 scopus 로고    scopus 로고
    • Only trans-epoxyesters were observed.
    • Only trans-epoxyesters were observed.
  • 24
    • 34547937290 scopus 로고    scopus 로고
    • In the presence of chalcone, a by-product (a mixture of isomers) resulting from the conjugate addition of enolate to chalcone was also formed
    • In the presence of chalcone, a by-product (a mixture of isomers) resulting from the conjugate addition of enolate to chalcone was also formed.
  • 25
    • 0028822867 scopus 로고    scopus 로고
    • The preparation of O-tert-butyldimethylsilyl lactaldehyde was performed according to: Marshall, J. A.; Shiping, X. J. Org. Chem. 1995, 60, 7230-7237.
    • The preparation of O-tert-butyldimethylsilyl lactaldehyde was performed according to: Marshall, J. A.; Shiping, X. J. Org. Chem. 1995, 60, 7230-7237.
  • 26
    • 0000471716 scopus 로고    scopus 로고
    • Preparation of tert-butylhydroperoxide solution: Hill, J. G.; Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607-3608.
    • Preparation of tert-butylhydroperoxide solution: Hill, J. G.; Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607-3608.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.