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Volumn 55, Issue 26, 1999, Pages 8025-8038

Synthesis of bicyclic proline analogs using a formal [3+2] intramolecular aziridine-allylsilane cycloaddition reaction

Author keywords

Aziridines; Bicyclic heterocyclic compounds; Nitrogen heterocycles; Silicon and compounds

Indexed keywords

ANALGESIC AGENT; ENZYME INHIBITOR; PROLINE DERIVATIVE;

EID: 0033603641     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00425-1     Document Type: Article
Times cited : (52)

References (38)
  • 7
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    • Toward rationally designed peptidyl-prolyl isomerase inhibitors
    • Abell, A. Ed.; JAI Press, Inc.; Greenwich, Connecticut
    • 4. (a) Germanas, J.P.; Kim, K.; Dumas, J.P. Toward Rationally Designed Peptidyl-prolyl Isomerase Inhibitors. In Advances in Amino Acid Mimetics and Peptidomimetics, Abell, A. Ed.; JAI Press, Inc.; Greenwich, Connecticut, Vol. 1, 1997, 233-250.
    • (1997) Advances in Amino Acid Mimetics and Peptidomimetics , vol.1 , pp. 233-250
    • Germanas, J.P.1    Kim, K.2    Dumas, J.P.3
  • 10
    • 0032564612 scopus 로고    scopus 로고
    • and references cited therein
    • 5. Other types of proline analogs such as the molecule shown below have been synthesized. Compounds of this type that lack a free NH and are usually intended to be dipeptide analogs of Gly·Pro have been prepared, see reference 4a. (equation presented) Other proline analogs with various substitution patterns on the pyrrolidine ring have also been reported. For example, see: Wang, Q.; Sasaki, N. A.; Potier, P. Tetrahedron 1998, 54, 15759-15780. and references cited therein.
    • (1998) Tetrahedron , vol.54 , pp. 15759-15780
    • Wang, Q.1    Sasaki, N.A.2    Potier, P.3
  • 15
    • 0030592795 scopus 로고    scopus 로고
    • 9. The intermolecular reaction of an aryl aziridine with an allyltrimethylsilane has recently been shown to produce the [3+2] annulation product, although the reaction is very limited in that only the p-chloro phenyl aziridine can be used in this intermolecular reaction. See: Schneider, M.R.; Mann, A.;. Taddei, M. Tetrahedron Lett. 1996, 37, 8493-8496.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8493-8496
    • Schneider, M.R.1    Mann, A.2    Taddei, M.3
  • 18
    • 33751391619 scopus 로고
    • For examples of the 3+2 annulation reaction with α,β-unsaturated carbonyl compounds see: (c)Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097.
    • (1992) J. Org. Chem. , vol.57 , pp. 6094-6097
    • Danheiser, R.L.1    Dixon, B.R.2    Gleason, R.W.3
  • 21
    • 0013633725 scopus 로고    scopus 로고
    • 11. For comprehensive reviews of this reaction see (a) Fleming, I. Chemtracts 1996, 1-64.
    • (1996) Chemtracts , pp. 1-64
    • Fleming, I.1
  • 23
    • 85064604194 scopus 로고
    • 12c have been reported which offer a good balance between retention during the annulation and ease of oxidative removal, however, these silanes are not commerically available. (a) Knolker, H. -J.; Wanzl, G. Synlett 1995, 378-382.
    • (1995) Synlett , pp. 378-382
    • Knolker, H.-J.1    Wanzl, G.2
  • 32
    • 0000414496 scopus 로고
    • The Mitsunobu reaction
    • Paquette, L. Eds.; John Wiley & Sons, Inc; New York
    • (b) Huges, D.L. The Mitsunobu Reaction. In Organic Reactions, Paquette, L. Eds.; John Wiley & Sons, Inc; New York, Vol.42, 1992, 335-636.
    • (1992) Organic Reactions , vol.42 , pp. 335-636
    • Huges, D.L.1
  • 33
    • 0030861232 scopus 로고    scopus 로고
    • Ni) the stereochemical integrity of the displacement is very high. For examples see: (a) Dauban, P.; Dodd, R.H.; J. Org. Chem. 1997, 62, 4277-4284.
    • (1997) J. Org. Chem. , vol.62 , pp. 4277-4284
    • Dauban, P.1    Dodd, R.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.