메뉴 건너뛰기




Volumn 45, Issue 11, 2004, Pages 2399-2402

A novel method for the preparation of benzylidenecyclohexanes with high optical purity

Author keywords

Asymmetric synthesis; Carbanion; Chiral olefin; Enantioselective substitution

Indexed keywords

ACETAL DERIVATIVE; BENZYLIDENE DERIVATIVE; CHLORINE DERIVATIVE; CYCLOHEXANE DERIVATIVE; METHANESULFONYL CHLORIDE; OXAZOLINE DERIVATIVE; SELENIUM DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 1242315555     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.099     Document Type: Article
Times cited : (16)

References (50)
  • 15
    • 3242866355 scopus 로고    scopus 로고
    • For reviews of diastereoselective Wittig type reactions, see:
    • For reviews of diastereoselective Wittig type reactions, see: Rein T., Reiser O. Acta Chem. Scandinavica. 50:1996;369-379.
    • (1996) Acta Chem. Scandinavica , vol.50 , pp. 369-379
    • Rein, T.1    Reiser, O.2
  • 33
    • 85030914444 scopus 로고    scopus 로고
    • note
    • 2O, 1a could be lithiated on treatment with n-BuLi without addition of a chiral ligand, giving 4 in high yield but with low enantioselectivity after addition of 3a and 4-tert-butylcyclohexanone.
  • 34
    • 85030894219 scopus 로고    scopus 로고
    • note
    • R 16.9 [(R)], and 19.0 [(S), 99% ee] min.
  • 35
    • 37049083405 scopus 로고
    • A good level of enantioselectivity has been reported in the reaction of non-dipole-stabilized α-seleno carbanions through a dynamic thermodynamic resolution pathway, see: Klute W., Dress R., Hoffmann R.W. J. Chem. Soc., Perkin Trans. 2. 1993;1409-1411.
    • (1993) J. Chem. Soc., Perkin Trans. 2 , pp. 1409-1411
    • Klute, W.1    Dress, R.2    Hoffmann, R.W.3
  • 38
    • 85030906971 scopus 로고    scopus 로고
    • note
    • We have demonstrated that the enantioselective reaction of the α-thio carbanion derived from benzyl phenyl sulfide proceeds through a dynamic kinetic resolution pathway; see Ref. 10. The reaction of the α-seleno carbanion derived from benzyl phenyl selenide was confirmed to proceed through a dynamic thermodynamic resolution pathway, showing that the α-seleno carbanion is configurationally more stable than the α-thio carbanion. The results will be published in due course.
  • 39
    • 85030912598 scopus 로고    scopus 로고
    • note
    • The reaction of 1b taking a longer time for lithiation resulted in lower yield of the product.
  • 40
    • 85030914001 scopus 로고    scopus 로고
    • note
    • We also examined the enantioselective reaction of 2-pyridyl selenide with 4-substituted cyclohexanone, but the obtained diastereomeric mixture could not be separated by column chromatography.
  • 43
    • 37049134143 scopus 로고
    • For conversion of β-selenoalcohols to alkenes, see:
    • For conversion of β-selenoalcohols to alkenes, see: Reich H.J., Chow F. J. Chem. Soc., Chem. Commun. 1975;790-791.
    • (1975) J. Chem. Soc., Chem. Commun. , pp. 790-791
    • Reich, H.J.1    Chow, F.2
  • 48
    • 49349139760 scopus 로고
    • For reviews, see:
    • For reviews, see: Clive D.L.J. Tetrahedron. 34:1978;1049-1132.
    • (1978) Tetrahedron , vol.34 , pp. 1049-1132
    • Clive, D.L.J.1
  • 49
  • 50
    • 85030903207 scopus 로고    scopus 로고
    • note
    • R 28.7 [ (M)-9 , 99% ee], and 33.4 [ (P) -9 ] min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.