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Volumn , Issue 9, 1998, Pages 1823-1832

The importance of electrostatic interactions in the stereoselective 1,3-dipolar cycloadditions of nitrones to chiral allyl ethers: An experimental and force field approach

Author keywords

1,3 Dipolar cycloadditions; Chiral allyl ethers; Nitrones; Transition state modeling

Indexed keywords


EID: 0001708378     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199809)1998:9<1823::AID-EJOC1823>3.0.CO;2-H     Document Type: Article
Times cited : (29)

References (36)
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    • (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications
    • R. Annunziata, M. Benaglia, M Cinquini, F. Cozzi, L. Raimondi, in Electronic Conference on Heterocyclic Chemistry (ECHET96). (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications, 1996 (see also: http://www.ch.ic.ac.uk/ectoc/echet96/papers/026/index.htm). CD-ROM included in J. Chem. Soc., Chem. Commun 1997, no. 6. Very recently, the attribution of the syn 4,4′ relative stereochemistry was confirmed on similar compounds via X-Ray analysis: M. Martín-Vilà. N. Hanafi, J. M. Jiménez, A. Alvarez-Lorena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuño, J. Org. Chem 1998, 63, 3581.
    • (1996) Electronic Conference on Heterocyclic Chemistry (ECHET96)
    • Annunziata, R.1    Benaglia, M.2    Cinquini, M.3    Cozzi, F.4    Raimondi, L.5
  • 11
    • 0038613987 scopus 로고    scopus 로고
    • R. Annunziata, M. Benaglia, M Cinquini, F. Cozzi, L. Raimondi, in Electronic Conference on Heterocyclic Chemistry (ECHET96). (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications, 1996 (see also: http://www.ch.ic.ac.uk/ectoc/echet96/papers/026/index.htm). CD-ROM included in J. Chem. Soc., Chem. Commun 1997, no. 6. Very recently, the attribution of the syn 4,4′ relative stereochemistry was confirmed on similar compounds via X-Ray analysis: M. Martín-Vilà. N. Hanafi, J. M. Jiménez, A. Alvarez-Lorena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuño, J. Org. Chem 1998, 63, 3581.
  • 12
    • 0038613987 scopus 로고    scopus 로고
    • R. Annunziata, M. Benaglia, M Cinquini, F. Cozzi, L. Raimondi, in Electronic Conference on Heterocyclic Chemistry (ECHET96). (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications, 1996 (see also: http://www.ch.ic.ac.uk/ectoc/echet96/papers/026/index.htm). CD-ROM included in J. Chem. Soc., Chem. Commun 1997, no. 6. Very recently, the attribution of the syn 4,4′ relative stereochemistry was confirmed on similar compounds via X-Ray analysis: M. Martín-Vilà. N. Hanafi, J. M. Jiménez, A. Alvarez-Lorena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuño, J. Org. Chem 1998, 63, 3581.
    • (1997) J. Chem. Soc., Chem. Commun , vol.6
  • 13
    • 0038613987 scopus 로고    scopus 로고
    • R. Annunziata, M. Benaglia, M Cinquini, F. Cozzi, L. Raimondi, in Electronic Conference on Heterocyclic Chemistry (ECHET96). (Eds.: H. R. Rzepa, J. Syndner). (CD-ROM); Royal Society of Chemistry Publications, 1996 (see also: http://www.ch.ic.ac.uk/ectoc/echet96/papers/026/index.htm). CD-ROM included in J. Chem. Soc., Chem. Commun 1997, no. 6. Very recently, the attribution of the syn 4,4′ relative stereochemistry was confirmed on similar compounds via X-Ray analysis: M. Martín-Vilà. N. Hanafi, J. M. Jiménez, A. Alvarez-Lorena, J. F. Piniella, V. Branchadell, A. Oliva, R. M. Ortuño, J. Org. Chem 1998, 63, 3581.
    • (1998) J. Org. Chem , vol.63 , pp. 3581
    • Martín-Vilà, M.1    Hanafi, N.2    Jiménez, J.M.3    Alvarez-Lorena, A.4    Piniella, J.F.5    Branchadell, V.6    Oliva, A.7    Ortuño, R.M.8
  • 17
    • 2842574998 scopus 로고    scopus 로고
    • note
    • The inside alkoxy cycloadduct features a 5,5′-syn (not anti) relative configuration because of the different priorities of the substituents at the C-5.
  • 18
    • 33845283500 scopus 로고
    • All cycloadditions were performed in benzene as solvent (Experimental Section and note 20) Alkene 3 was reacted with formaldehyde N-benzylnitrone in DMSO as solvent (80°C, 2 h, 50%). The diastereoisomeric ratio (15a/b ≥ 85:15) was the same observed for the reaction performed in benzene, thus ruling out the presence of an hydrogen bond within the reactants in the TS. The presence of a H bond between the OH and the π bond in the ground state conformation of allylic alcohols was suggested: S. D. Kahn, C. F. Pau, A. R. Chamberlin, W. J. Hehre J. Am. Chem. Soc. 1987, 109, 650.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 650
    • Kahn, S.D.1    Pau, C.F.2    Chamberlin, A.R.3    Hehre, W.J.4
  • 20
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    • Unpublished results from our laboratories
    • [11b] Unpublished results from our laboratories.
  • 24
    • 0030734550 scopus 로고    scopus 로고
    • [14b] For a recent study on Michael-type addition to (E)- and (Z)-γ-alkoxy-α,β-unsaturated esters leading to a prevalence of syn adducts, see:Y. Xiang, H.-J. Gi, D. Niu, R. F. Schinazi, K. Zhao, J. Org. Chem. 1997, 62, 7430.
    • (1997) J. Org. Chem. , vol.62 , pp. 7430
    • Xiang, Y.1    Gi, H.-J.2    Niu, D.3    Schinazi, R.F.4    Zhao, K.5
  • 27
    • 0003323222 scopus 로고
    • Molecular Mechanics
    • American Chemical Society; Washington D.C.
    • U. Burkert, N. L. Allinger, Molecular Mechanics. ACS Monograph 177; American Chemical Society; Washington D.C., 1982.
    • (1982) ACS Monograph 177
    • Burkert, U.1    Allinger, N.L.2
  • 31
    • 2842573876 scopus 로고    scopus 로고
    • note
    • Cycloaddition reactions were performed in benzene on a reduced scale. Special care is needed, since this solvent is known to be highly toxic and carcinogenic.
  • 35
    • 2842599329 scopus 로고    scopus 로고
    • MacroModel substructures can be obtained directly from the authors (e-mail: laura@iumchz.chimorg.unimi.it)
    • MacroModel substructures can be obtained directly from the authors (e-mail: laura@iumchz.chimorg.unimi.it).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.