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Volumn 69, Issue 21, 2004, Pages 7004-7012

Diastereoselective [2+2]-cycloaddition reactions of unsymmetrical cyclic ketenes with imines: Synthesis of modified prolines and theoretical study of the reaction mechanism

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; DERIVATIVES; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

EID: 5444227205     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040163w     Document Type: Article
Times cited : (57)

References (39)
  • 1
    • 0037504191 scopus 로고    scopus 로고
    • For a recent review see: Kotha, S. Acc. Chem. Res. 2003, 36, 342-351.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 342-351
    • Kotha, S.1
  • 3
    • 0037152608 scopus 로고    scopus 로고
    • The synthetic methodology for the synthesis of cyclic amino acid derivatives has been extensively reviewed: Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
    • (2002) Tetrahedron , vol.58 , pp. 8629-8659
    • Park, K.-H.1    Kurth, M.J.2
  • 11
    • 0002674759 scopus 로고
    • Georg, G. I., Ed.;, VCH Publishers: New York
    • For a review of the synthetic utility of the ketene-imine cycloaddition, see: Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.;, VCH Publishers: New York, 1993; pp 295-368.
    • (1993) The Organic Chemistry of β-Lactams , pp. 295-368
    • Georg, G.I.1    Ravikumar, V.T.2
  • 22
    • 0019932198 scopus 로고
    • N-p-Methoxyphenylbenzaldimine was used, as it allows easy oxidative removal of the p-methoxyphenyl group, with ammonium cerium (IV) nitrate, to give the N-unsubstituted β-lactam, as shown in: Kronenthal, D. R.; Han, C. Y.; Taylor M. K. J. Org. Chem. 1982, 47, 2765.
    • (1982) J. Org. Chem. , vol.47 , pp. 2765
    • Kronenthal, D.R.1    Han, C.Y.2    Taylor, M.K.3
  • 25
    • 5444257295 scopus 로고    scopus 로고
    • note
    • 3 (c 0.7), are +134.0 and -134.0, respectively.
  • 26
    • 5444236252 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of 15a (and therefore 15b) was studied by NMR (NOESY spectra), and was confirmed to be cis, thus excluding a possible epimerization of the carbon atom C3 (see Suporting Information).
  • 33
    • 0001398447 scopus 로고
    • For a description of the torquoelectronic effect, see: (a) Rondan, G. N.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2099
    • Rondan, G.N.1    Houk, K.N.2
  • 39
    • 0942277395 scopus 로고    scopus 로고
    • (b) A survey of the use of MTPA as chiral derivatizing agent can be found in: Seco, J. M.; Quiñoá, E.; Riguera, R. Chem. Rev. 2004, 104, 17.
    • (2004) Chem. Rev. , vol.104 , pp. 17
    • Seco, J.M.1    Quiñoá, E.2    Riguera, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.