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Volumn 1, Issue 1, 1999, Pages 87-90

Selective lithiation of 2-methyloxazoles. Applications to pivotal bond constructions in the phorboxazole nucleus

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DERIVATIVE; OXAZOLE DERIVATIVE;

EID: 0033565015     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990027r     Document Type: Article
Times cited : (69)

References (40)
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    • and references therein
    • (b) Cocito, C. Microbiol. Rev. 1979, 43, 145-198 and references therein.
    • (1979) Microbiol. Rev. , vol.43 , pp. 145-198
    • Cocito, C.1
  • 17
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    • The carbanion of 2 may be delocalized into the C=N π system
    • The carbanion of 2 may be delocalized into the C=N π system.
  • 21
    • 0001498230 scopus 로고
    • (d) Iddon, B. Heterocycles 1994, 37, 1321-1346.
    • (1994) Heterocycles , vol.37 , pp. 1321-1346
    • Iddon, B.1
  • 22
  • 29
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    • Dilithiated 3-methylthiophene-2-carboxylic acid has been reported to give a different distribution of regioisomers with alkyl bromides than with other electrophiles (acetone, methyl iodide, and deuterium oxide): Gould, N. P.; Lee, T.-J. J. Org. Chem. 1980, 45, 4530-4532.
    • (1980) J. Org. Chem. , vol.45 , pp. 4530-4532
    • Gould, N.P.1    Lee, T.-J.2
  • 30
    • 85034128585 scopus 로고    scopus 로고
    • note
    • 1H NMR to contain 6d as the only methylated product and ≤3% of the starting material 1d.
  • 31
    • 0000861392 scopus 로고
    • Knaus, G.; Meyers, A. I. J. Org. Chem. 1974, 39, 1192-1195. This study did not report the use of lithium diethylamide.
    • (1974) J. Org. Chem. , vol.39 , pp. 1192-1195
    • Knaus, G.1    Meyers, A.I.2
  • 35
    • 85034137516 scopus 로고    scopus 로고
    • The details of the synthesis of fragments 10 and 11 will be reported in due course
    • The details of the synthesis of fragments 10 and 11 will be reported in due course.
  • 36
    • 85034150704 scopus 로고    scopus 로고
    • note
    • 1H NMR has allowed the observation of distinct intermediates consistent with 2 and 3 as well as their complete equilibration to 2. Analysis of the products 6 and 7 formed upon quenching these reactions suggests that ring alkylation of 2 is not occurring. For more details, see the Supporting Information.
  • 37
    • 0001426580 scopus 로고
    • This conclusion is supported by the results of Fraser et al., who have reported that the rate of proton exchange between amines and lithiated amides decreases with increasing steric bulk: Fraser, R. R.; Baignee, A.; Bresse, M.; Hata, K. Tetrahedron Lett. 1982, 23, 4195-4198.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 4195-4198
    • Fraser, R.R.1    Baignee, A.2    Bresse, M.3    Hata, K.4
  • 38
    • 85034133270 scopus 로고    scopus 로고
    • It cannot be ruled out that the kinetic selectivity of lithium diethylamide favors the formation of 2
    • It cannot be ruled out that the kinetic selectivity of lithium diethylamide favors the formation of 2.
  • 39
    • 85034138400 scopus 로고    scopus 로고
    • 1H NMR
    • 1H NMR.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.