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Volumn 41, Issue 9, 2000, Pages 1359-1362

Synthesis of highly epimerizable N-protected α-amino aldehydes of high enantiomeric excess

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; AMINOALDEHYDE; OXIDIZING AGENT;

EID: 0034716554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02293-5     Document Type: Article
Times cited : (105)

References (26)
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    • (e)
    • (e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162.
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    • Reetz, M.T.1
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    • 0000285544 scopus 로고
    • For other examples of N-protected phenylglycinal derivatives, see: (a)
    • For other examples of N-protected phenylglycinal derivatives, see: (a) Matsunaga, N.; Harada, H.; Aoyama, T.; Shioiri, T. Heterocycles 1992, 33, 235-255.
    • (1992) Heterocycles , vol.33 , pp. 235-255
    • Matsunaga, N.1    Harada, H.2    Aoyama, T.3    Shioiri, T.4
  • 15
    • 0026669060 scopus 로고
    • For comparison of the TEMPO and Swern procedures, see:
    • Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029-5032. For comparison of the TEMPO and Swern procedures, see: Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051-6064.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5029-5032
    • Leanna, M.R.1    Sowin, T.J.2    Morton, H.E.3
  • 16
    • 0032575218 scopus 로고    scopus 로고
    • Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029-5032. For comparison of the TEMPO and Swern procedures, see: Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051-6064.
    • (1998) Tetrahedron , vol.54 , pp. 6051-6064
    • Jurczak, J.1    Gryko, D.2    Kobrzycka, E.3    Gruza, H.4    Prokopowicz, P.5
  • 17
    • 0343775206 scopus 로고    scopus 로고
    • For a prior example employing sodium borohydride in the reduction of phenylglycinal derivatives, see Ref. 6
    • For a prior example employing sodium borohydride in the reduction of phenylglycinal derivatives, see Ref. 6.
  • 18
    • 0033546262 scopus 로고    scopus 로고
    • Frigerio, M.; Santagostino M.; Sputore S.J.
    • 2-Iodoxybenzoic acid was prepared by oxidation of 2-iodobenzoic acid according to a recently reported procedure 2-Iodoxybenzoic acid was transformed to the Dess-Martin periodinane following the Ireland protocol
    • 2-Iodoxybenzoic acid was prepared by oxidation of 2-iodobenzoic acid according to a recently reported procedure: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. 2-Iodoxybenzoic acid was transformed to the Dess-Martin periodinane following the Ireland protocol: Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
    • (1999) Org. Chem. , vol.64 , pp. 4537-4538
  • 19
    • 33751384984 scopus 로고
    • 2-Iodoxybenzoic acid was prepared by oxidation of 2-iodobenzoic acid according to a recently reported procedure: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. 2-Iodoxybenzoic acid was transformed to the Dess-Martin periodinane following the Ireland protocol: Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
    • (1993) , vol.58 , pp. 2899
    • Ireland, R.E.1    Liu, L.J.2    Org., Chem.3
  • 21
    • 0001755016 scopus 로고    scopus 로고
    • The superiority of the Dess-Martin periodinane for the preparation of chiral α-fluoro aldehydes has been documented:
    • The superiority of the Dess-Martin periodinane for the preparation of chiral α-fluoro aldehydes has been documented: Davis, F. A.; Kasu, P. V. N.; Sundarababu, G.; Qi, H. J. Org. Chem. 1997, 62, 7546-7547.
    • (1997) J. Org. Chem. , vol.62 , pp. 7546-7547
    • Davis, F.A.1    Kasu, P.V.N.2    Sundarababu, G.3    Qi, H.4
  • 24
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    • For leading references, see: Gross, E.; Meienhofer, J., Eds.; Academic: New York Chapter 7.
    • For leading references, see: Kemp, D. S. In The Peptides; Gross, E.; Meienhofer, J., Eds.; Academic: New York, 1979; Volume 1, Chapter 7.
    • (1979) In the Peptides , vol.1
    • Kemp, D.S.1
  • 25
    • 0019947041 scopus 로고
    • For the preparation of N-Boc and N-Cbz alaninal in ees ranging from 82-99%, using TEMPO, Swern, or Parikh-Doering oxidations, see: Ref. 8, and
    • For the preparation of N-Boc and N-Cbz alaninal in ees ranging from 82-99%, using TEMPO, Swern, or Parikh-Doering oxidations, see: Ref. 8, and Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 1921-1924.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 1921-1924
    • Hamada, Y.1    Shioiri, T.2
  • 26
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    • Note
    • R(N-Fmoc-(R)-phenylglycinol)=24.5 min) established an ee of 99%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.