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Volumn 56, Issue 23, 2015, Pages 3428-3430

Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis

Author keywords

Asymmetric catalysis; Chlorination; Hydrogen bonding; Non covalent interactions; Organocatalysis

Indexed keywords

ESTER DERIVATIVE; KETENE DERIVATIVE; N CHLOROSUCCINIMIDE; SILYL KETENE ACETAL DERIVATIVE; SUCCINIMIDE DERIVATIVE; TERTIARY ALPHA CHLORO ESTER DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84929957260     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.01.124     Document Type: Article
Times cited : (36)

References (41)
  • 1
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    • For recent reviews on enantioselective α-halogenation reactions including chlorination, see
    • For recent reviews on enantioselective α-halogenation reactions including chlorination, see: M. Oestreich Angew. Chem., Int. Ed. 44 2005 2324 2327
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 2324-2327
    • Oestreich, M.1
  • 12
    • 0033790769 scopus 로고    scopus 로고
    • To our knowledge, aside from the few examples cited in Refs. 5-7, the only catalytic α-chlorination reactions producing enantioenriched tertiary alkyl chlorides employ 1,3-dicarbonyl and 1,3-ketophosphonate substrates. For representative references, see
    • To our knowledge, aside from the few examples cited in Refs. 5-7, the only catalytic α-chlorination reactions producing enantioenriched tertiary alkyl chlorides employ 1,3-dicarbonyl and 1,3-ketophosphonate substrates. For representative references, see: L. Hintermann, and A. Togni Helv. Chem. Acta 83 2000 2425 2435
    • (2000) Helv. Chem. Acta , vol.83 , pp. 2425-2435
    • Hintermann, L.1    Togni, A.2
  • 20
    • 79956352398 scopus 로고    scopus 로고
    • Enantioselective chlorination at C3 of 3-substituted oxindoles has been reported. For representative references, see
    • Enantioselective chlorination at C3 of 3-substituted oxindoles has been reported. For representative references, see: M.-X. Zhao, Z.-W. Zhang, M.-X. Chen, W.-H. Tang, and M. Shi Eur. J. Org. Chem. 2011 3001 3008
    • (2011) Eur. J. Org. Chem. , pp. 3001-3008
    • Zhao, M.-X.1    Zhang, Z.-W.2    Chen, M.-X.3    Tang, W.-H.4    Shi, M.5
  • 23
    • 0035925178 scopus 로고    scopus 로고
    • Enantioselective synthesis of alkyl chlorides from ketenes has been reported. For representative references, see
    • Enantioselective synthesis of alkyl chlorides from ketenes has been reported. For representative references, see: H. Wack, A.E. Taggi, A.M. Hafez, W.J. Drury, and T. Lectka J. Am. Chem. Soc. 123 2001 1531 1532
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1531-1532
    • Wack, H.1    Taggi, A.E.2    Hafez, A.M.3    Drury, W.J.4    Lectka, T.5
  • 26
    • 9344239378 scopus 로고    scopus 로고
    • For an example of enantioselective α-chlorination using Lewis acid catalysis with a chiral chlorinating reagent, see
    • For an example of enantioselective α-chlorination using Lewis acid catalysis with a chiral chlorinating reagent, see: Y. Zhang, K. Shibatomi, and H. Yamamoto J. Am. Chem. Soc. 126 2004 15038 15039
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15038-15039
    • Zhang, Y.1    Shibatomi, K.2    Yamamoto, H.3
  • 34
    • 77950805314 scopus 로고    scopus 로고
    • For examples of reactions where cation-π interaction is proposed to be involved in selectivity and correlated with size of catalyst arene, see
    • For examples of reactions where cation-π interaction is proposed to be involved in selectivity and correlated with size of catalyst arene, see: R.R. Knowles, S. Lin, and E.N. Jacobsen J. Am. Chem. Soc. 132 2010 5030 5032
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5030-5032
    • Knowles, R.R.1    Lin, S.2    Jacobsen, E.N.3
  • 37
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    • For examples of stereospecific substitution reactions on α-chloro-1,3-dicarbonyl compounds, see Ref. 4g. For studies of stereospecific substitution on tertiary halides, see
    • For examples of stereospecific substitution reactions on α-chloro-1,3-dicarbonyl compounds, see Ref. 4g. For studies of stereospecific substitution on tertiary halides, see: S. Winstein, S. Smint, and D. Darwish Tetrahedron Lett. 1 1959 24 31
    • (1959) Tetrahedron Lett. , vol.1 , pp. 24-31
    • Winstein, S.1    Smint, S.2    Darwish, D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.