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Volumn 55, Issue 18, 1999, Pages 5853-5866

Regio- and stereoselectivity in the cyclization of enolates derived from 4,5-, 5,6-, and 6,7-epoxy-1-phenyl-1-alkanones. Competition between C- and O- alkylation

Author keywords

[No Author keywords available]

Indexed keywords

4,5 EPOXY 1 PHENYL 1 ALKANONE; 5,6 EPOXY 1 PHENYL 1 ALKANONE; 6,7 EPOXY 1 PHENYL 1 ALKANONE; ALKANE DERIVATIVE; ALKANONE; ENOLATE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033617237     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00226-4     Document Type: Article
Times cited : (25)

References (33)
  • 1
    • 85037455306 scopus 로고
    • and references therein
    • 1. Gorzynski, S. J. Synthesis, 1984, 629-656 and references therein.
    • (1984) Synthesis , pp. 629-656
    • Gorzynski, S.J.1
  • 8
    • 0001564641 scopus 로고
    • For other related procedures, see also: d) Gaoni, Y. Tetrahedron, 1972, 28, 5525-5531.
    • (1972) Tetrahedron , vol.28 , pp. 5525-5531
    • Gaoni, Y.1
  • 11
    • 0027376442 scopus 로고
    • 6. Dechoux, L.; Ebel, M.; Jung, L.; Stambach, J. F. Tetrahedron Lett. 1993, 34, 7405-7408. In some cases, we were unable to achieve the high yields and results reported in the article (entries 3, 6 and 10, Table)
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7405-7408
    • Dechoux, L.1    Ebel, M.2    Jung, L.3    Stambach, J.F.4
  • 15
    • 0013538902 scopus 로고    scopus 로고
    • note
    • 9. The intermediate trans bromohydrins were not separated pure, but directly cyclized to the corresponding epoxides
  • 17
    • 0013536254 scopus 로고    scopus 로고
    • note
    • 4 the geometry of the enolate has no influence on the regio-or stereochemical result of the addition reaction. In the case of 10a,b, the obtainment of 14a,b and 15a,b in the cyclization reaction points to the exclusive formation of the corresponding (Z)-enolate 22a,b (Scheme 3).
  • 18
    • 0013504724 scopus 로고    scopus 로고
    • note
    • 12. The epimerization of 12a,b into 13a,b and vice versa under acidic or basic conditions, respectively, can reasonably be rationalized by means of a retro cyclization process through the protonated γ-HK 26a,b and epoxy enol 27a,b (acidic conditions) and alcoholate 28a,b and epoxy enolate 21a,b (basic conditions). The metal chelation between the enolate and the oxirane oxygens favors the cis γ-HK 12a,b under basic conditions. (Formula Presented)
  • 19
    • 0013507620 scopus 로고    scopus 로고
    • note
    • 13. It has to be stressed that, in the present study, four-membered cyclic γ-HKs were never formed in these reactions, independently of the type of the starting epoxy ketones and reaction conditions used.
  • 20
    • 0013540102 scopus 로고    scopus 로고
    • note
    • 15
  • 23
    • 0013468374 scopus 로고    scopus 로고
    • note
    • 4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.