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Volumn 45, Issue 9, 2004, Pages 1845-1848

Phase-transfer-catalyzed asymmetric Darzens reaction using a new chiral ammonium salt

Author keywords

Asymmetric synthesis; Darzens reaction; Phase transfer

Indexed keywords

AMIDE; AMMONIA;

EID: 1242338935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.009     Document Type: Article
Times cited : (59)

References (27)
  • 1
    • 0003795882 scopus 로고    scopus 로고
    • For books on PTC, see: M.E. Halpern. Washington, DC: American Chemical Society
    • For books on PTC, see: Halpern M.E. Phase-Transfer Catalysis. Mechanism and Synthesis. 1997;American Chemical Society, Washington, DC.
    • (1997) Phase-Transfer Catalysis. Mechanism and Synthesis
  • 2
    • 0003795884 scopus 로고    scopus 로고
    • Y. Sasson, & R. Neumann. London: Blackie A. & M.
    • Sasson Y., Neumann R. Handbook of Phase-Transfer Catalysis. 1997;Blackie A. & M. London.
    • (1997) Handbook of Phase-Transfer Catalysis
  • 3
    • 0033152728 scopus 로고    scopus 로고
    • For a review, see:
    • For a review, see: Nelson A. Angew Chem. Int. Ed. 38:1999;1583-1585.
    • (1999) Angew Chem. Int. Ed. , vol.38 , pp. 1583-1585
    • Nelson, A.1
  • 9
    • 0000784042 scopus 로고
    • For a review, see: B.M. Trost, I. Fleming, Heathcock C.H. Oxford: Pergamon
    • For a review, see: Rosen T. Trost B.M., Fleming I., Heathcock C.H. Comprehensive Organic Synthesis. 2:1991;409 Pergamon, Oxford.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 409
    • Rosen, T.1
  • 10
    • 0001851157 scopus 로고    scopus 로고
    • For some examples of the asymmetric Darzens reaction using chiral auxiliary or external ligands, see:
    • For some examples of the asymmetric Darzens reaction using chiral auxiliary or external ligands, see: Ohkata K., Shinohara Y., Takagi R., Hiraga Y. Chem. Commun. 1996;2411-2412.
    • (1996) Chem. Commun. , pp. 2411-2412
    • Ohkata, K.1    Shinohara, Y.2    Takagi, R.3    Hiraga, Y.4
  • 12
    • 0037189887 scopus 로고    scopus 로고
    • For an excellent result using a chiral sulfone amide, see:
    • For an excellent result using a chiral sulfone amide, see: Aggarwal V.K., Hynd G., Picoul W., Vasse J.-L. J. Am. Chem. Soc. 124:2002;9964-9965.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9964-9965
    • Aggarwal, V.K.1    Hynd, G.2    Picoul, W.3    Vasse, J.-L.4
  • 19
    • 0035955210 scopus 로고    scopus 로고
    • For successful examples via catalytic asymmetric epoxidation, see:
    • For successful examples via catalytic asymmetric epoxidation, see: Nemoto T., Ohshima T., Shibasaki M. J. Am. Chem. Soc. 123:2001;9474-9475.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9474-9475
    • Nemoto, T.1    Ohshima, T.2    Shibasaki, M.3
  • 23
    • 85030901735 scopus 로고    scopus 로고
    • note
    • 3 and MeOH however toluene and THF are not easy to be dissolved.
  • 24
    • 85030897502 scopus 로고    scopus 로고
    • note
    • R: 10.3 min (major) and 12.5 min (minor), respectively.
  • 25
    • 85030903152 scopus 로고    scopus 로고
    • note
    • However derivatives of PTC A were investigated, any attempts to introduce substituents on aromatic rings and quaternary ammonium moieties gave unsatisfactory results in enantiomeric excess.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.