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Volumn 65, Issue 5, 2000, Pages 1590-1596

1,3-Dipolar cycloaddition of furfuryl nitrones with acrylates. A convenient approach to protected 4-hydroxypyroglutamic acids

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; NITRONE DERIVATIVE;

EID: 0034629360     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991560n     Document Type: Article
Times cited : (55)

References (68)
  • 9
  • 51
    • 33847567338 scopus 로고    scopus 로고
    • note
    • The authors have deposited atomic coordinates for the structure of 2a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
  • 57
    • 0001285069 scopus 로고    scopus 로고
    • Several comparative studies have suggested semiempirical methods as a good choice for studying cycloaddition processes involving chiral substrates. See: (a) Sbai, A.; Branchadell, V.; Ortuno, R. M.; Oliva, A. J. Org. Chem. 1997, 62, 3049-3054.
    • (1997) J. Org. Chem. , vol.62 , pp. 3049-3054
    • Sbai, A.1    Branchadell, V.2    Ortuno, R.M.3    Oliva, A.4
  • 59
    • 33847550420 scopus 로고    scopus 로고
    • Semiempirical geometry optimizations for all systems were carried out at the AMI and PM3 levels of theory as implemented in WINMOPAC 2.0. Fujitsu Limited. 1998. For simplicity, the W-benzyl group of the nitrone 2a was replaced with a methyl group.
    • Semiempirical geometry optimizations for all systems were carried out at the AMI and PM3 levels of theory as implemented in WINMOPAC 2.0. Fujitsu Limited. 1998. For simplicity, the W-benzyl group of the nitrone 2a was replaced with a methyl group.
  • 61
    • 33847536722 scopus 로고    scopus 로고
    • note
    • After tedious Chromatographie separations enriched mixtures of diastereomers could be obtained in order to identify selected signals from the NMR spectra (see the Experimental Section). Nevertheless, subsequent reduction-cyclization to diastereomeric pyrrolidin-2-ones afforded separable mixtures of isomers.
  • 62
    • 33847539173 scopus 로고    scopus 로고
    • See the Supporting Information for the detailed discussion.
    • See the Supporting Information for the detailed discussion.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.