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Volumn 52, Issue 19, 2011, Pages 2501-2504

Tactics for the asymmetric preparation of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane scaffolds

Author keywords

Aminocyclopropanes; Chiral auxiliaries; Kulinkovich de Meijere reaction; Organotitanium chemistry; Polonovski reaction

Indexed keywords

2 AZABICYCLO[3.1.0]HEXANE; 2 AZABICYCLO[4.1.0]HEPTANE; HEPTANE DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

EID: 79953680225     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.026     Document Type: Article
Times cited : (9)

References (49)
  • 16
    • 36549002124 scopus 로고    scopus 로고
    • For recent examples of alternative methods for the synthesis of fused bicyclic aminocyclopropane derivatives, see: S. Couty, C. Meyer, and J. Cossy Synlett 2007 2819 2822
    • (2007) Synlett , pp. 2819-2822
    • Couty, S.1    Meyer, C.2    Cossy, J.3
  • 26
    • 84913355472 scopus 로고    scopus 로고
    • Thèse de l'Université Pierre et Marie Curie, Paris
    • Ouizem, S. Ph.D. Dissertation, Thse de l'Université Pierre et Marie Curie, Paris, 2010.
    • (2010) Ph.D. Dissertation
    • Ouizem, S.1
  • 30
    • 79953723864 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 802584 and 802585. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.Uk ).
  • 33
    • 0000515042 scopus 로고
    • Conversion of a phenylglycinol moiety into a β-amino phenylsulfide, which is then treated with LiDBB: A.I. Meyers, and L.E. Burgess J. Org. Chem. 56 1991 2294 2296
    • (1991) J. Org. Chem. , vol.56 , pp. 2294-2296
    • Meyers, A.I.1    Burgess, L.E.2
  • 39
    • 0030665617 scopus 로고    scopus 로고
    • Conversion of a phenylglycinol moiety into a mesylate, which is then submitted to an elimination reaction: O. Fains, and J.M. Vernon Tetrahedron Lett. 38 1997 8265 8266
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8265-8266
    • Fains, O.1    Vernon, J.M.2
  • 40
    • 0035858740 scopus 로고    scopus 로고
    • Conversion of a phenylglycinol moiety into an arylselenide, which is then oxidised to trigger an elimination reaction: R.A. Bragg, J. Clayden, M. Bladon, and O. Ichihara Tetrahedron Lett. 42 2001 3411 3414
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3411-3414
    • Bragg, R.A.1    Clayden, J.2    Bladon, M.3    Ichihara, O.4
  • 42
    • 79953718876 scopus 로고    scopus 로고
    • In e-EROS Encyclopedia of Reagents for Organic Synthesis
    • Paquette L. A., Ed.-in-Chief; John Wiley & Sons, Ltd.; article doi: 10.1002/047084289X.rp203
    • Caine, D. In e-EROS Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.-in-Chief; John Wiley & Sons, Ltd.; article "Potassium t-Butoxide-Dimethyl Sulfoxide" doi: 10.1002/047084289X. rp203.
    • Potassium T-Butoxide-Dimethyl Sulfoxide
    • Caine, D.1
  • 44
    • 17744395123 scopus 로고    scopus 로고
    • T. Vilaivan, C. Winotapan, V. Banphavichit, T. Shinada, and Y. Ohfune J. Org. Chem. 70 2005 3464 3471 As is reported in this article, the allylation reaction proceeds with much higher diastereoselectivity (98:2) using the same imine substituted with a 2-hydroxy-1-phenylethyl group rather than a 2-methoxy-1-phenylethyl group. We nonetheless chose the latter, because we were hoping we would be able to separate the diastereoisomers of the homoallylamine products, or of the corresponding acetamides 3f. This would have enabled us to synthesise both enantiomers of the secondary cyclopropylamine 1f.
    • (2005) J. Org. Chem. , vol.70 , pp. 3464-3471
    • Vilaivan, T.1    Winotapan, C.2    Banphavichit, V.3    Shinada, T.4    Ohfune, Y.5
  • 45
    • 79953714710 scopus 로고    scopus 로고
    • note
    • 3 at reflux.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.