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Volumn 45, Issue 6, 2006, Pages 935-938

Dimerization of lithiated terminal aziridines

Author keywords

Aziridines; Lithiation; Small ring systems; Synthetic methods

Indexed keywords

CATALYSTS; DIMERIZATION; ENZYMES; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 32044436336     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503303     Document Type: Article
Times cited : (32)

References (41)
  • 5
    • 18244376859 scopus 로고    scopus 로고
    • The electrophile trapping of lithiated terminal aziridines has been developed recently, see: D. M. Hodgson, P. G. Humphreys, J. G. Ward, Org. Lett. 2005, 7, 1153-1156.
    • (2005) Org. Lett. , vol.7 , pp. 1153-1156
    • Hodgson, D.M.1    Humphreys, P.G.2    Ward, J.G.3
  • 6
    • 0033714636 scopus 로고    scopus 로고
    • see Ref. [13]
    • For a review of the utility of diamine derivatives in asymmetric catalysis, see: F. Fache, E. Schulz, M. L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231: for the utility of 1,4-diamine derivatives as HIV protease inhibitors, see Ref. [13].
    • (2000) Chem. Rev. , vol.100 , pp. 2159-2231
    • Fache, F.1    Schulz, E.2    Tommasino, M.L.3    Lemaire, M.4
  • 7
    • 8244240969 scopus 로고
    • Dimerization of a lithiated methylene aziridine to give a cyclopentene has been reported, see: H. Quast, C. A. W. Vélez, Angew. Chem. 1974, 86, 380-381;
    • (1974) Angew. Chem. , vol.86 , pp. 380-381
    • Quast, H.1    Vélez, C.A.W.2
  • 9
    • 0344118032 scopus 로고    scopus 로고
    • dimerization of N-unprotected aziridines under Lewis acid catalysis to give aminoaziridines is known, see: A. Caiazzo, S. Dalili, A. K. Yudin, Synlett 2003, 2198-2202.
    • (2003) Synlett , pp. 2198-2202
    • Caiazzo, A.1    Dalili, S.2    Yudin, A.K.3
  • 21
    • 32044449798 scopus 로고    scopus 로고
    • note
    • In studies with substrate 4a, the use of fewer equivalents of LTMP or extended reaction times at -78°C led to incomplete reaction.
  • 30
    • 0038336897 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 2718-2736;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2718-2736
  • 32
    • 32044447429 scopus 로고    scopus 로고
    • note
    • Conversely, when 2,3-epoxypropylbenzene was subjected to dimerization conditions (see Experimental Section) the major product was cinnamyl alcohol (arising from benzylic deprotonation and eliminative rearrangement), and no significant 2-ene-1,4-diol was observed.
  • 33
    • 0028900966 scopus 로고
    • Similar dihydroxylation of the analogous N-Boc-protected 2-ene-1,4-diamine displayed poor diastercoselectivity (2:3) and favored the opposite (less desirable for HIV protease inhibition) diastereoisomer to that seen in our case, see: a) A. V. R. Rao, M. K. Gurjar, S. Pal, R. J. Pariza, M. S. Chorghade, Tetrahedron Lett. 1995, 36, 2505-2508;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2505-2508
    • Rao, A.V.R.1    Gurjar, M.K.2    Pal, S.3    Pariza, R.J.4    Chorghade, M.S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.