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Tetrahedron Letters
Volumn 25, Issue 5, 1984, Pages 495-498
Highly selective, kinetically controlled enolate formation using lithium dialkylamides in the presence of trimethylchlorosilane
Author keywords

[No Author keywords available]
Indexed keywords

EID: 0001113382     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)99920-9     Document Type: Article
Times cited : (355)
References (16)
  • 1
    • 84908816577 scopus 로고
    • The synthesis of di-t-alkylamines is described in the accompanying paper; see also, Harvard University
    • (1983) Ph.D. dissertation
    • Gross1
  • 5
    • 33845550671 scopus 로고
    • After completion of this work the TMSCl in situ trapping of α-lithiated cyanobenzene was reported.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6155
    • Krizan1    Martin2
  • 6
    • 84918406705 scopus 로고    scopus 로고
    • All product ratios were determined by VPC and comparison with authentic samples.
  • 8
    • 33847799021 scopus 로고
    • Base-catalyzed .beta.-elimination reactions. VI. Elimination from tert-butyl 3-(para-substituted phenoxy)- and 3-(para-substituted benzoyloxy)thiolpropionates in 45% (weight/weight) dioxane-water
    • While exclusive formation of the KC enolate in the reaction of LDA with 2-octanone is reported, only a 54% yield was obtained. Attempts to repeat this work gave a 94:6 ratio of the kinetically and thermodynamically controlled enol ethers in ca. 50% yield.
    • (1976) The Journal of Organic Chemistry , vol.41 , pp. 1369
    • Clark1    Heathcock2
  • 9
    • 0001570202 scopus 로고
    • A directing effect of neighboring aromatic groups on the regiochemistry of formation and stereochemistry of alkylation and bromination of ketone lithium enolates. Evidence for lithium-arene coordination and dramatic effect of copper(I) in controlling stereochemistry and limiting polyalkylation
    • (1979) Journal of the American Chemical Society , vol.104 , pp. 934
    • Posner1    Lentz2
  • 12
    • 84918406704 scopus 로고    scopus 로고
    • 3, and filtered into an NMR tube.
  • 13
    • 84918406703 scopus 로고    scopus 로고
    • This argument ignores the repulsion of L and R′ in IV. The presence of the pericyclic transition states in the presence of HMPA is also in question.
  • 14
    • 33847086723 scopus 로고
    • Role of HMPT and TMEDA in control of enolate stereochemistry for reactions of lithium amides with 3-pentanone
    • Rathke has suggested that enolate formation in the presence of HMPA was thermodynamically controlled on the basis that high base to ketone ratios gave increased amounts of the E enolate.
    • (1980) Journal of the American Chemical Society , vol.102 , pp. 3960
    • Fataftah1    Kopka2    Rathke3
  • 15
    • 84918406702 scopus 로고    scopus 로고
    • The reactions were performed by adding LOBA to the ketone and a 10-fold excess of TMSCl in 23% HMPA/THF at −78°. Therefore, the occurrence of some equilibration prior to trapping is possible. The preferred mode of addition, ketone added to LOBA and TMSCl, was not feasible since LOBA reacts with TMSCl at −78° in the presence of HMPA.
  • 16
    • 84918406701 scopus 로고    scopus 로고
    • This research was assisted financially by a grant from the National Science Foundation.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.