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Volumn 2, Issue 2, 2004, Pages 157-159

The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSTS; HYDROGENATION; ISOMERS; REDUCTION; STEREOCHEMISTRY; SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 1642388423     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b312552a     Document Type: Article
Times cited : (73)

References (32)
  • 3
    • 0032795262 scopus 로고    scopus 로고
    • We prefer to describe these conversions as Michael addition reactions rather than Friedel-Crafts processes since the pyrrole nitrogen can also add to an acrylate tethered through C2 of this five-membered heterocycle (see, for example, M. G. Banwell, A. M. Bray, A. C. Willis and D. J. Wong, New J. Chem., 1999, 23, 687).
    • (1999) New J. Chem. , vol.23 , pp. 687
    • Banwell, M.G.1    Bray, A.M.2    Willis, A.C.3    Wong, D.J.4
  • 4
    • 25544436935 scopus 로고
    • and references cited therein
    • See, for example, R. Lueoend and R. Neier, Helv. Chim. Acta, 1991, 74, 91 and references cited therein.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 91
    • Lueoend, R.1    Neier, R.2
  • 5
    • 0023883293 scopus 로고
    • (-)-8-Phenylmenthyl dimethyl phosphonoacetate (see H. J. Gais, G. Schmiedl, W. A. Ball, J. Bund, G. Hellmann and I. Erdelmeier, Tetrahedron Lett., 1988, 29, 1773) was used for the conversion 9→10 whilst commercially available trimethyl phosphonoacetate was used for the conversion 9→11.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1773
    • Gais, H.J.1    Schmiedl, G.2    Ball, W.A.3    Bund, J.4    Hellmann, G.5    Erdelmeier, I.6
  • 8
    • 0016850334 scopus 로고
    • (-)-8-Phenylmenthyl acrylate required in the preparation of compound 10 was obtained by the method of E. J. Corey and H. E. Ensley, J. Am. Chem. Soc., 1975, 97, 6908.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 6908
    • Corey, E.J.1    Ensley, H.E.2
  • 13
    • 1642496074 scopus 로고    scopus 로고
    • note
    • 9 but subsequently confirmed by chemical correlation studies (see text).
  • 14
    • 1642455057 scopus 로고    scopus 로고
    • note
    • This material was purchased from TCI, Japan.
  • 18
    • 1642455058 scopus 로고    scopus 로고
    • note
    • t (major enantiomer): 12.2 min; (minor enantiomer): 14.8 min.
  • 19
    • 1642536823 scopus 로고    scopus 로고
    • note
    • t (major enantiomer): 12.3 min; (minor enantiomer): 14.9 min.
  • 21
    • 0033936085 scopus 로고    scopus 로고
    • and references cited therein
    • For an excellent review of the applications of these complexes in synthesis see; (b) J. S. Johnson and D. A. Evans, Acc. Chem. Res., 2000, 33, 325 and references cited therein.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 325
    • Johnson, J.S.1    Evans, D.A.2
  • 24
    • 1642455059 scopus 로고    scopus 로고
    • note
    • t (major enantiomer): 15.3 min; (minor enantiomer): 13.6 min.
  • 30
    • 0036192333 scopus 로고    scopus 로고
    • 3 see: (b) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Tetrahedron Lett., 2001, 42, 8063; (c) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Synthesis, 2001, 2165.
    • (2002) Synlett , pp. 531
    • Babu, S.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.