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Volumn 49, Issue 42, 2008, Pages 6065-6067

Substituent stereochemistry effects on diastereoselective methylation reaction of 4-chloroadamantan-2-ones

Author keywords

Adamantane; Carbonyl compound; Diastereoselectivity; Nucleophilic addition; Organocerium reagent

Indexed keywords

4 CHLOROADAMANTAN 2 ONE DERIVATIVE; AMANTADINE DERIVATIVE; CERIUM; CHLORIDE; CHLORINE; UNCLASSIFIED DRUG;

EID: 50549096857     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.181     Document Type: Article
Times cited : (6)

References (45)
  • 2
    • 50549085982 scopus 로고    scopus 로고
    • Chen, C. S. H.; Shen, D. -M.; Wentzek, S. E. PCT Int. Appl. WO09428.885, 1994.
    • Chen, C. S. H.; Shen, D. -M.; Wentzek, S. E. PCT Int. Appl. WO09428.885, 1994.
  • 24
    • 50549085636 scopus 로고    scopus 로고
    • note
    • 7a
  • 25
    • 50549086766 scopus 로고    scopus 로고
    • note
    • The numbering of the adamantane carbons not necessarily conforms to IUPAC nomenclature. For better comparison, however, we employed a numbering which is consistent throughout irregardless of the substituents. The term axial (ax) and equatorial (eq) denote the stereochemical position of the substituent with respect to the six-membered ring bearing the highest number of substituents.
  • 28
    • 38849195303 scopus 로고
    • Spectroscopical data of compounds 1 and 2 are identical to those previously reported by:
    • Spectroscopical data of compounds 1 and 2 are identical to those previously reported by:. Janku J., Burkhard J., and Vodička L. Collect. Czech. Chem. Commun. 52 (1987) 2028-2035
    • (1987) Collect. Czech. Chem. Commun. , vol.52 , pp. 2028-2035
    • Janku, J.1    Burkhard, J.2    Vodička, L.3
  • 30
    • 50549085072 scopus 로고    scopus 로고
    • note
    • 4. After filtration, the organic solvent was distilled and the crude product was purified by chromatography column (petroleum ether-EtOAc, 20:1) for giving 0.18 g (0.92 mmol) of 4(ax)-chloro-2(ax)-hydroxy-2(eq)-methyladamantane (3). This value (yield 85%) refers to isolated compound after chromatographic purification taking heed of removal of the solvent. The procedure has required atmospheric pressure distillation because distillation of the solvent on a rotary evaporator caused losses of material due to the volatility of the adamantane derivative product.
  • 33
    • 50549091281 scopus 로고    scopus 로고
    • note
    • 3, 100 MHz): δ = 25.84 (C-7), 27.05 (C-9), 27.21 (Me), 34.85 (C-8), 35.75 (C-5), 36.10 (C-10), 38.47 (C-1), 39.28 (C-6), 44.33 (C-3), 68.76 (C-4), 74.64 (C-2).
  • 35
    • 50549087019 scopus 로고    scopus 로고
    • note
    • The major products identified by GC-MS were a dehalogenated compound and a tetracyclic compound.
  • 41
    • 0000271524 scopus 로고
    • It is desirable to use the Grignard reagent as the source of transferable methyl group, which was purchased as solution in THF and titrated just before use:
    • It is desirable to use the Grignard reagent as the source of transferable methyl group, which was purchased as solution in THF and titrated just before use:. Bergbreit D.E., and Pendergrass E. J. Org. Chem. 46 (1981) 219-220
    • (1981) J. Org. Chem. , vol.46 , pp. 219-220
    • Bergbreit, D.E.1    Pendergrass, E.2
  • 43
    • 0005821348 scopus 로고
    • and references cited therein
    • Johnson C.R., and Tait B.D. J. Org. Chem. 52 (1987) 281-283 and references cited therein
    • (1987) J. Org. Chem. , vol.52 , pp. 281-283
    • Johnson, C.R.1    Tait, B.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.