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Volumn 74, Issue 2, 2009, Pages 696-702

Enantiocontrolled synthesis of polychlorinated hydrocarbon motifs: A nucleophilic multiple chlorination process revisited

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; CHIRAL EPOXIDES; HALOGEN ATOMS; MOLECULAR SCAFFOLDS; N-CHLOROSUCCINIMIDE; ONE STEPS; REAGENT SYSTEMS;

EID: 59049103973     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802093d     Document Type: Article
Times cited : (52)

References (32)
  • 1
    • 4944226169 scopus 로고    scopus 로고
    • For pertinent reviews on natural halogenated compounds, see: a
    • For pertinent reviews on natural halogenated compounds, see: (a) Gribble, G. W. J. Chem. Educ. 2004, 81, 1441-1449.
    • (2004) J. Chem. Educ , vol.81 , pp. 1441-1449
    • Gribble, G.W.1
  • 2
    • 34147164504 scopus 로고    scopus 로고
    • (b) Gribble, G. W. Am. Sci. 2004, 92, 342-349.
    • (2004) Am. Sci , vol.92 , pp. 342-349
    • Gribble, G.W.1
  • 8
    • 0000055068 scopus 로고    scopus 로고
    • For synthetic studies on bioactive polyhalogenated natural compounds, see: a
    • For synthetic studies on bioactive polyhalogenated natural compounds, see: (a) Jung, M. E.; Parker, M. H. J. Org. Chem. 1997, 62, 7094-7095.
    • (1997) J. Org. Chem , vol.62 , pp. 7094-7095
    • Jung, M.E.1    Parker, M.H.2
  • 24
    • 0014932590 scopus 로고
    • For pioneering studies on this class of molecules, see: a
    • For pioneering studies on this class of molecules, see: (a) Elovson, J.; Vagelos, P. R. Biochemistry 1970, 9, 3110-3126.
    • (1970) Biochemistry , vol.9 , pp. 3110-3126
    • Elovson, J.1    Vagelos, P.R.2
  • 30
    • 2942702061 scopus 로고    scopus 로고
    • For recent reviews on enantioselective halogenations, see: a
    • For recent reviews on enantioselective halogenations, see: (a) Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147-1155.
    • (2004) Chem. Commun , pp. 1147-1155
    • Ibrahim, H.1    Togni, A.2
  • 32
    • 64549091381 scopus 로고    scopus 로고
    • The stereochemistry of each chloroalkene (6a and 6b) was unambiguously confirmed by NOE experiments. The selective production of 3-chloro-substituted alkene is presumably attributed to the preferential attack of a chlorideion at the less hindered site where interaction with the bulky tert-butyldiphenylsilyl substituent is avoidable.SRSR
    • The stereochemistry of each chloroalkene (6a and 6b) was unambiguously confirmed by NOE experiments. The selective production of 3-chloro-substituted alkene is presumably attributed to the preferential attack of a chlorideion at the less hindered site where interaction with the bulky tert-butyldiphenylsilyl substituent is avoidable.SRSR


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.