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Volumn 8, Issue 4, 2010, Pages 864-872

MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis: The cycloaddition approach

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CYCLOADDITION;

EID: 76249085894     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b918612c     Document Type: Article
Times cited : (26)

References (35)
  • 2
  • 18
    • 33646589039 scopus 로고    scopus 로고
    • For other enantiopure cyclic nitrones see the review
    • P.-F. Wang P. Gao P.-F. Xu Synlett 2006 1095 1099
    • (2006) Synlett , pp. 1095-1099
    • Wang, P.-F.1    Gao, P.2    Xu, P.-F.3
  • 29
    • 0029026529 scopus 로고
    • int: 0.09; refinement vs.F; final R values (observed data): R = 0.0533, wR = 0.0867. For the ORTEP drawing of 1, see ESI The reaction between MiPNO and cyclohexene, sluggish in toluene, was also performed in a polar solvent, NMP, without any improvement: 48 h, 64% conversion The stereochemistry of the cycloadducts was assigned on the basis of their NOESY spectra Such a ring opening was previously reported:
    • E. Marcantoni M. Petrini O. Polimanti Tetrahedron Lett. 1995 36 3561 3562
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3561-3562
    • Marcantoni, E.1    Petrini, M.2    Polimanti, O.3
  • 30
    • 0027244183 scopus 로고
    • Attempted NOESY experiments were not conclusive enough to allow determination of the relative configuration of the minor isomer
    • A. Padwa M. Meske Z. Ni Tetrahedron Lett. 1993 34 5047 5050
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5047-5050
    • Padwa, A.1    Meske, M.2    Ni, Z.3
  • 31
    • 59949098435 scopus 로고    scopus 로고
    • int: 0.07; refinement vs. F; final R values (observed data): R = 0.0531, wR = 0.0921. The relative streochemistry (R) at C5 was attributed knowing the (S) configuration at C11 from the starting material Moc-Phe-OH Note that this step produces only volatile side products (3-methyl-butanone and methylamine) For related compounds, see:
    • O. N. Burchak C. Philouze P. Y. Chavant S. Py Org. Lett. 2008 10 3021 3023
    • (2008) Org. Lett. , vol.10 , pp. 3021-3023
    • Burchak, O.N.1    Philouze, C.2    Chavant, P.Y.3    Py, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.