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Volumn 46, Issue 16, 2010, Pages 2835-2837

The intramolecular amination of allenes

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; AMINE; AMINOCYCLOPROPANE; NUCLEOPHILE; PROPANE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77950515119     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b926179f     Document Type: Article
Times cited : (42)

References (54)
  • 3
    • 77950497107 scopus 로고    scopus 로고
    • University of Oxford, This account focuses on the reactions of sulfamate substrates; details of analogous reactions with carbamate substrates, that behave quite differently, will be published separately:
    • S. L. Kostiuk, Chemistry Part II Thesis, University of Oxford, 2006
    • (2006) Chemistry Part II Thesis
    • Kostiuk, S.L.1
  • 38
    • 61349122654 scopus 로고    scopus 로고
    • Methylene aziridines are only rarely prepared by allene aziridination:
    • T. Yoshimitsu T. Ino T. Tanaka Org. Lett. 2008 10 5457
    • (2008) Org. Lett. , vol.10 , pp. 5457
    • Yoshimitsu, T.1    Ino, T.2    Tanaka, T.3
  • 42
    • 3042816129 scopus 로고    scopus 로고
    • Blakey's group has studied analogous reactions of alkynyl sulfamates and has very recently extended those studies to encompass allenyl substrates to generate 1-alkyl-1-aminocyclopropanes:
    • J. J. Shiers M. Shipman J. F. Hayes A. M. Z. Slawin J. Am. Chem. Soc. 2004 126 6868
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 6868
    • Shiers, J.J.1    Shipman, M.2    Hayes, J.F.3    Slawin, A.M.Z.4
  • 48
    • 0034835815 scopus 로고    scopus 로고
    • Inclusion of one mole equivalent of propyl sulfamate in the reaction mixture with substrate 3 did not result in intermolecular amination, the allene being returned unchanged after work-up It is possible that the intermediate iminocyclopropane in this case survives the reaction conditions, by virtue of the presence of the iso-propyl group, and is hydrated during product isolation Assuming the reaction to follow the pathway suggested in Scheme 2, rotation of the terminal methyl-bearing carbon away from the N-bound dirhodium ligand, upon amination, would generate a U-shaped methyl,ethyl-substituted allyl cation that would be expected to close in a disrotatory fashion, giving rise to the observed (NOESY) stereochemistry
    • C. G. Espino P. M. Wehn J. Chow J. Du Bois J. Am. Chem. Soc. 2001 123 6935
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6935
    • Espino, C.G.1    Wehn, P.M.2    Chow, J.3    Du Bois, J.4
  • 50
    • 9644254037 scopus 로고    scopus 로고
    • 3CN solution of each substrate was subjected to microwave heating first at 100 °C and then at 120 °C for 10-20 minutesat each temperature Quast first demonstrated the thermal interconversion of methylene aziridines and iminocyclopropanes, and showed that the latter cycloreverted rapidly to alkene and isocyanide at 190 °C:
    • C. G. Espino K. W. Fiori M. Kim J. Du Bois J. Am. Chem. Soc. 2004 126 15378
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15378
    • Espino, C.G.1    Fiori, K.W.2    Kim, M.3    Du Bois, J.4
  • 52
    • 0001895395 scopus 로고
    • The transformation 24 → 26 is analogous to the well-known reactions of chloroenamines with nucleophiles resulting in aminocyclopropane derivatives; for leading early work see:
    • M. T. Reetz J. Rheinheimer J. Org. Chem. 1986 51 5465
    • (1986) J. Org. Chem. , vol.51 , pp. 5465
    • Reetz, M.T.1    Rheinheimer, J.2
  • 53
    • 2342608830 scopus 로고
    • Related reactions are described for example in ref. 19 and subsequent papers; however, apart from the examples in ref. 8c, we are aware of just a single paper describing the α-substitutions of 1-(N-sulfonylamino)-1- oxycyclopropane substrates:
    • J. Szmuszkovicz E. Cerda M. F. Grostic J. F. Zieserl, Jr. Tetrahedron Lett. 1967 8 3969
    • (1967) Tetrahedron Lett. , vol.8 , pp. 3969
    • Szmuszkovicz, J.1    Cerda, E.2    Grostic, M.F.3    Zieserl Jr., J.F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.