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Volumn 27, Issue 5, 1986, Pages 531-534

Stereoselective deprotonation of α,β-unsaturated amides

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Indexed keywords


EID: 46149140335     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)84032-0     Document Type: Article
Times cited : (18)

References (46)
  • 12
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    • A modified Ireland model which accentuates energetic and orientation non-eguivalence of carbonyl oxygen lone pairs in coordination with base has been advanced, but its necessity has been questioned.
    • (1982) Tetrahedron Lett. , pp. 4119
    • Narula1
  • 20
    • 0016777504 scopus 로고
    • Exceptions to this statement concern the stereoselective Z-methyl deprotonation of ethyl 3-methylbut-2-enoate as established by Claisen rearrangement of the resulting dienolate
    • (1975) J. Org. Chem. , vol.40 , pp. 3309
    • Wilson1    Myers2
  • 21
    • 0010582437 scopus 로고
    • and the study of stereoselective deprotonation of unsaturated tosyl hydrazones during the Shapiro reaction, We are very grateful to Dr. G.I. Feutrill, University of Melbourne, Australia for providing the last reference.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 3414
    • Dauben1    Rivers2    l3
  • 23
    • 84942709251 scopus 로고
    • A Note on Stereochemical Observations of the Deprotonation of Ethyl 2-Alkenoates
    • (1981) Helvetica Chimica Acta , vol.64 , pp. 1023
    • Krebs1
  • 26
    • 0001229094 scopus 로고
    • This work, including studies on ester 3b, was first announced at the 66th CIC Conference, Calgary, Canada, June 5 – 8, 1983, Abstr. OR 21-2. In order to avoid overlap we exclude presentation ofour results on 3b which are in complete agreement with those reported by Harris and Weiler
    • (1982) J. Org. Chem. , vol.47 , pp. 163
    • Kende1    Toder2
  • 27
    • 84942709251 scopus 로고
    • A Note on Stereochemical Observations of the Deprotonation of Ethyl 2-Alkenoates
    • (1981) Helvetica Chimica Acta , vol.64 , pp. 1023
    • Krebs1
  • 28
    • 84918448441 scopus 로고    scopus 로고
    • Preparation: Green, J.R.; Majewski, M.; Alo, B.I.; Snieckus, V. Tetrahedron Lett. accompanying communication.
  • 30
    • 84918448440 scopus 로고    scopus 로고
    • Prepared by stereoselective deuteration of the copper dienolate of N,N-dimethyl 3-methylbut-2-enamide.
  • 32
    • 0001677992 scopus 로고
    • Prepared from N,N-dimethyl acetoacetamide according to Weiler's excellent procedure:
    • (1979) Can. J. Chem. , vol.57 , pp. 1431
    • Sum1    Weiler2
  • 35
    • 84918448439 scopus 로고    scopus 로고
    • This result agrees qualitatively with that reported for the analogous 3a in which a kinetic isotope effect was also observed.
  • 36
    • 33947085723 scopus 로고
    • Conformational analysis by lanthanide induced shifts. I. Applications to .alpha.,.beta.-unsaturated aldehydes, ketones, esters, and amides
    • s-is-:s-trans conformer population ratios of substituted α,β-unsaturated ketones, esters, and amides determined by the LIS method favor substantially s-cis forms:
    • (1973) Journal of the American Chemical Society , vol.95 , pp. 6365
    • Montando1    Librando2    Caccamese3    Maravingna4
  • 37
    • 34250237140 scopus 로고
    • The phenomenon of amide to lithium ion association has been thoroughly documented:
    • (1981) Monatsh. Chem. , vol.112 , pp. 25
    • Fuchs1    Rode2
  • 39
    • 10244250625 scopus 로고
    • Eight-membered ring transition states are involved in certain proton transfer reactions
    • (1983) Tetrahedron Lett. , pp. 569
    • Wilson1    Price2
  • 42
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    • 1,2 -stereochemistry.
  • 44
    • 84918448437 scopus 로고    scopus 로고
    • 24 in which, as suggested, conformational energies determine the stereochemical outcome.
  • 45
    • 0001030975 scopus 로고
    • Additional evidence for the significance of conformational effects in enolate formation has been very recently reported
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1440
    • Chamberlin1    Reich2
  • 46
    • 84918448436 scopus 로고    scopus 로고
    • We are grateful to NSERC Canada for continuing financial support. J.R.G. is a Science 67 Scholarship awardee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.