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Volumn 75, Issue 8, 2010, Pages 2645-2650

A Straightforward Three-Component Synthesis of α-Amino Esters Containing a Phenylalanine or a Phenylglycine Scaffold

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; BENZYLIC; CONCISE SYNTHESIS; ETHYL GLYOXYLATE; HIGH YIELD; IN-SITU; ORGANOZINC REAGENTS; PHENYLGLYCINES; SECONDARY AMINES; THREE COMPONENT REACTIONS; THREE-COMPONENT;

EID: 77951002240     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1002328     Document Type: Article
Times cited : (53)

References (74)
  • 1
    • 8344249465 scopus 로고    scopus 로고
    • For some selected examples, see
    • For some selected examples, see: Sardina, J. F.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872
    • (1996) Chem. Rev. , vol.96 , pp. 1825-1872
    • Sardina, J.F.1    Rapoport, H.2
  • 6
    • 0037043180 scopus 로고    scopus 로고
    • List, B. Tetrahedron 2002, 58, 5573-5590
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 29
    • 84918022463 scopus 로고
    • Besides the Petasis or the Ugi reaction, the Strecker reaction might be relevant for the synthesis of α-amino acids through preliminary preparation of α-aminonitriles. For some exemples, see
    • Besides the Petasis or the Ugi reaction, the Strecker reaction might be relevant for the synthesis of α-amino acids through preliminary preparation of α-aminonitriles. For some exemples, see: Strecker, A. Justus Liebigs Ann. Chem. 1850, 75, 27-51
    • (1850) Justus Liebigs Ann. Chem. , vol.75 , pp. 27-51
    • Strecker, A.1
  • 48
    • 77950971159 scopus 로고    scopus 로고
    • The Petasis reaction leads to α-amino acids with high yields. However, reaction times are generally important, and the reaction does not tolerate the presence of some electron-withdrawing groups connected to phenyl moieties. The Ugi reaction requires the use of cleavable isocyanides and a further hydrolysis step
    • The Petasis reaction leads to α-amino acids with high yields. However, reaction times are generally important, and the reaction does not tolerate the presence of some electron-withdrawing groups connected to phenyl moieties. The Ugi reaction requires the use of cleavable isocyanides and a further hydrolysis step.
  • 55
    • 77950997315 scopus 로고    scopus 로고
    • Organozinc reagents are alkaline compounds
    • Organozinc reagents are alkaline compounds.
  • 56
    • 77950997628 scopus 로고    scopus 로고
    • It was mentioned in previous works that at least 2 equiv of the organozinc compound are required for the reaction to proceed efficiently
    • It was mentioned in previous works that at least 2 equiv of the organozinc compound are required for the reaction to proceed efficiently.
  • 57
    • 77951010913 scopus 로고    scopus 로고
    • Although an exothermic reaction tends to develop, the temperature of the medium was not controlled. As a consequence, this rise of the medium temperature is sufficient to avoid a preliminary heating of ethyl glyoxylate (which is generally known to require a depolymerization step prior to use)
    • Although an exothermic reaction tends to develop, the temperature of the medium was not controlled. As a consequence, this rise of the medium temperature is sufficient to avoid a preliminary heating of ethyl glyoxylate (which is generally known to require a depolymerization step prior to use).
  • 60
    • 77950983951 scopus 로고    scopus 로고
    • Piperazine derivatives generally furnish coupling products in lower yields. This behavior has already been observed in other studies conducted in our laboratory
    • Piperazine derivatives generally furnish coupling products in lower yields. This behavior has already been observed in other studies conducted in our laboratory.
  • 64
    • 0034625424 scopus 로고    scopus 로고
    • For a review of additions to N -acyliminium ions
    • For a review of additions to N -acyliminium ions, see: Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817-3856
    • (2000) Tetrahedron , vol.56 , pp. 3817-3856
    • Speckamp, W.N.1    Moolenaar, M.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.