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Volumn , Issue 13, 2005, Pages 2694-2701

Tandem addition/cyclization of alkynylzinc reagents to enantiopure 2-tert-butyl-3,5-dimethyl-2,3-dihydroimidazol-4-one N-oxide: Potential precursors of quaternary α-amino acids

Author keywords

Alkynylzinc; Amino acids; Cyclization; Dihydroisoxazole; Imidazolidinone; Nitrones

Indexed keywords


EID: 22144442445     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400861     Document Type: Article
Times cited : (49)

References (56)
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    • a corrigendum to this publication has been published in Angew. Chem. Int. Ed. Engl. 1986, 25, 766.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 766
  • 27
    • 22144464427 scopus 로고    scopus 로고
    • note
    • Not isolated. We propose the structure (2S)-2-terr-butyl-2-hydroxy-3- methyl-2,3-dihydroimidazol-4-one 1-oxide on the basis of NMR evidence.
  • 29
    • 22144498070 scopus 로고    scopus 로고
    • note
    • For the NMR determination with O-acetylmandelic acid as chiral shift reagent, see the Exp. Sect.
  • 31
    • 0033537047 scopus 로고    scopus 로고
    • [19]) produced 2a in 95% ee from enantiopure 3a (see Exp. Sect.). [31] For nitrone alkynylation, see: D. E. Frantz, R. Faessler, E. M. Carreira, J. Am. Chem. Soc. 1999, 121, 11245-11246.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11245-11246
    • Frantz, D.E.1    Faessler, R.2    Carreira, E.M.3
  • 34
    • 2342468598 scopus 로고    scopus 로고
    • For recent examples of C=N bond alkynylation reactions, see: D. A. Black, B. A. Arndtsen, Org. Lett. 2004, 6, 1107-1110.
    • (2004) Org. Lett. , vol.6 , pp. 1107-1110
    • Black, D.A.1    Arndtsen, B.A.2
  • 39
    • 22144480072 scopus 로고    scopus 로고
    • note
    • We observed that when stoichiometric amounts of diethylzinc were present in the reaction of nitrones, trace amounts of the ethyl adduct were sometimes observed. Replacing diethylzinc with dimethylzinc suppressed this side reaction.
  • 40
    • 22144434711 scopus 로고    scopus 로고
    • note
    • [20]): see the last entry of Table 1.
  • 41
    • 22144475082 scopus 로고    scopus 로고
    • note
    • Under the same conditions, the reaction of 2a led mainly to decomposition products.
  • 42
    • 22144485155 scopus 로고    scopus 로고
    • See the Exp. Sect.
    • See the Exp. Sect.
  • 44
    • 22144485516 scopus 로고    scopus 로고
    • See the Exp. Sect.
    • See the Exp. Sect.
  • 45
    • 22144472933 scopus 로고    scopus 로고
    • note
    • Nevertheless, mass spectrometry indicated only 22% deuterium.
  • 55
    • 33751044609 scopus 로고
    • For IRC analysis, see: K. Fukui, Acc. Chem. Res. 1981, 14, 363-368.
    • (1981) Acc. Chem. Res. , vol.14 , pp. 363-368
    • Fukui, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.