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Volumn 69, Issue 19, 2004, Pages 6244-6248

Synthesis of chiral amino epoxyaziridines: Useful intermediates for the preparation of chiral trisubstituted piperidines

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; NUCLEAR MAGNETIC RESONANCE; ORGANIC POLYMERS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

EID: 4644287003     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0490806     Document Type: Article
Times cited : (28)

References (32)
  • 11
    • 77957031616 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego, CA, Chapter 3
    • (c) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1993; Vol. 44, Chapter 3, pp 189-256.
    • (1993) The Alkaloids , vol.44 , pp. 189-256
    • Takahata, H.1    Momose, T.2
  • 12
    • 77957037489 scopus 로고    scopus 로고
    • Pelletier, S. W., Ed.; Pergamon: Oxford, UK, Chapter 2
    • (d) Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, UK, 1996; Vol. 10, Chapter 2, pp 155-299.
    • (1996) Alkaloids: Chemical and Biological Perspectives , vol.10 , pp. 155-299
    • Schneider, M.J.1
  • 13
    • 0035807571 scopus 로고    scopus 로고
    • Some recent synthesis of hydroxylated piperidines: (a) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
    • (2001) Org. Lett. , vol.3 , pp. 3169
    • Davis, F.A.1    Chao, B.2    Rao, A.3
  • 24
    • 4644306848 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra (300 MHz) of compound 5.
  • 26
    • 0000763561 scopus 로고    scopus 로고
    • N,N-Dibenzylamino carbonyl compounds react with nucleophiles, in absence of Lewis acids, with a nonchelation control. See: Reetz, M. T. Chem. Rev. 1999, 99, 1121.
    • (1999) Chem. Rev. , vol.99 , pp. 1121
    • Reetz, M.T.1
  • 27
    • 4644240276 scopus 로고    scopus 로고
    • note
    • Synthesis of ketone 3 from 2 proceeded with no detectable racemization, which was determined by chiral HPLC in the synthesis of amino diepoxides from serine. See ref 5.
  • 28
    • 4644266802 scopus 로고    scopus 로고
    • note
    • No racemization is observed in the use of N,N-dibenzylamino carbonyl compounds as electrophiles. See ref 10.
  • 30
    • 0043076447 scopus 로고    scopus 로고
    • Previously, we studied the ring opening of nonactivated aminoaziridines with nucleophiles, using different acids [see: (a) Concellón, J. M.; Riego, E. J. Org. Chem. 2003, 68, 6407.
    • (2003) J. Org. Chem. , vol.68 , pp. 6407
    • Concellón, J.M.1    Riego, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.