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Volumn 64, Issue 17, 1999, Pages 6495-6498

Toward the development of a general chiral α-substituted acetate enolate synthon for aldolization. DMAP- and NET3-promoted oxazolidinethione 'deacylation'

Author keywords

[No Author keywords available]

Indexed keywords

ACETATE ENOLATE; ACETIC ACID DERIVATIVE; OXAZOLIDINE DERIVATIVE; OXAZOLIDINETHIONE; UNCLASSIFIED DRUG;

EID: 0033588392     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990444h     Document Type: Article
Times cited : (26)

References (31)
  • 2
    • 25744450449 scopus 로고
    • Specialist Periodical Reports; Royal Society of Chemistry: London
    • (b) Amino Acids, Peptides and proteins. Specialist Periodical Reports; Young, G. T., Sheppard, R. C., Ed.; Royal Society of Chemistry: London, 1968-1983; Vol. 1-16.
    • (1968) Amino Acids, Peptides and Proteins , vol.1-16
    • Young, G.T.1    Sheppard, R.C.2
  • 18
    • 0001541455 scopus 로고
    • 3 enolization, see: (a) Lehnert, W. Tetrahedron Lett. 1970, 11, 4723. (b) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4135. (c) Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211.
    • (1970) Tetrahedron Lett. , vol.11 , pp. 4723
    • Lehnert, W.1
  • 19
    • 0001473363 scopus 로고
    • 3 enolization, see: (a) Lehnert, W. Tetrahedron Lett. 1970, 11, 4723. (b) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4135. (c) Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4135
    • Harrison, C.R.1
  • 20
    • 0000183076 scopus 로고
    • 3 enolization, see: (a) Lehnert, W. Tetrahedron Lett. 1970, 11, 4723. (b) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4135. (c) Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5211
    • Brocchini, S.J.1    Eberle, M.2    Lawton, R.G.3
  • 21
    • 0000012047 scopus 로고
    • For representative titanium-mediated aldol-type reactions, see: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (b) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866. (c) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (c) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 5722
    • Siegel, C.1    Thornton, E.R.2
  • 22
    • 0025364262 scopus 로고
    • For representative titanium-mediated aldol-type reactions, see: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (b) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866. (c) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (c) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 866
    • Evans, D.A.1    Clark, J.S.2    Metternich, R.3    Novack, V.J.4    Sheppard, G.S.5
  • 23
    • 33748468588 scopus 로고
    • For representative titanium-mediated aldol-type reactions, see: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (b) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866. (c) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (c) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8215
    • Evans, D.A.1    Urpi, F.2    Somers, T.C.3    Clark, J.S.4    Bilodeau, M.T.5
  • 24
    • 84958315401 scopus 로고
    • For representative titanium-mediated aldol-type reactions, see: (a) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. (b) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866. (c) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (c) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1047
    • Evans, D.A.1    Rieger, D.L.2    Bilodeau, M.T.3    Urpi, F.4
  • 25
    • 0345424313 scopus 로고    scopus 로고
    • note
    • This α-bromo thioimide intermediate is unstable at 0 °C. Attempts to obtain pure N-(α-bromoacetyl)oxazoliduiethione from bromoacetyl chloride and oxazolidinethione 1 were not successful.
  • 29
    • 0024814717 scopus 로고
    • For previous asymmetric synthesis of hydroxyleucine, see: (a) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6637-6640
    • Jung, M.E.1    Jung, Y.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.