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Volumn 2015, Issue 14, 2015, Pages 3036-3039

Flow synthesis of fluorinated α-amino acids

Author keywords

Amines; Amino acids; Flow; Fluorine; Photochemistry

Indexed keywords


EID: 84928814014     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201500300     Document Type: Article
Times cited : (34)

References (57)
  • 18
    • 84899650866 scopus 로고    scopus 로고
    • Alternatively, alkyl side chains of α-amino esters can be directly fluorinated by using a photocatalyst. Regioselectivity is an issue, however, see:, Angew. Chem. 2014, 126, 4778 - 4781.
    • Alternatively, alkyl side chains of α-amino esters can be directly fluorinated by using a photocatalyst. Regioselectivity is an issue, however, see:, S. D. Halperin, H. Fan, S. Chang, R. E. Martin, R. Britton, Angew. Chem. Int. Ed. 2014, 53, 4690-4690; Angew. Chem. 2014, 126, 4778-4781.
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 4690-4690
    • Halperin, S.D.1    Fan, H.2    Chang, S.3    Martin, R.E.4    Britton, R.5
  • 22
    • 84928780854 scopus 로고    scopus 로고
    • For several recent reviews, see
    • For several recent reviews, see
  • 27
    • 84928807916 scopus 로고    scopus 로고
    • For the Strecker synthesis of α-CF3, α-amino acids, see
    • For the Strecker synthesis of α-CF3, α-amino acids, see
  • 36
    • 84928813545 scopus 로고    scopus 로고
    • For reviews on flow photochemistry, see
    • For reviews on flow photochemistry, see
  • 41
    • 84928817272 scopus 로고    scopus 로고
    • Dry compressed air (20.5?±?0.5?% O2 in N2) can also be used and gives similar yields of α-amino nitriles. See the Supporting Information for details.
    • Dry compressed air (20.5?±?0.5?% O2 in N2) can also be used and gives similar yields of α-amino nitriles. See the Supporting Information for details.
  • 42
    • 84928777183 scopus 로고    scopus 로고
    • See the Supporting Information for full experimental details.
    • See the Supporting Information for full experimental details.
  • 43
    • 84928811302 scopus 로고    scopus 로고
    • For data describing the relationship of photooxidation yield and lamp power, see Figures S1 and S2 in the Supporting Information.
    • For data describing the relationship of photooxidation yield and lamp power, see Figures S1 and S2 in the Supporting Information.
  • 44
    • 84928806475 scopus 로고    scopus 로고
    • Yield determined by 1H NMR spectroscopy with mesitylene as an internal standard.
    • Yield determined by 1H NMR spectroscopy with mesitylene as an internal standard.
  • 48
    • 84928777632 scopus 로고    scopus 로고
    • The solvent from the previous step, THF, must be removed due to its undesired reaction and consumption of HCl, forming 4-chlorobutan-1-ol.
    • The solvent from the previous step, THF, must be removed due to its undesired reaction and consumption of HCl, forming 4-chlorobutan-1-ol.
  • 49
    • 84928786236 scopus 로고    scopus 로고
    • The observed ratio of amino acid to ester was approximately 5:1.
    • The observed ratio of amino acid to ester was approximately 5:1.
  • 50
    • 84928810792 scopus 로고    scopus 로고
    • Aqueous work up was used to quench an excess of TMSCN and to remove TBAF. The yields of α-amino nitriles in 2-MeTHF were similar to those in THF.
    • Aqueous work up was used to quench an excess of TMSCN and to remove TBAF. The yields of α-amino nitriles in 2-MeTHF were similar to those in THF.
  • 51
    • 84928798640 scopus 로고    scopus 로고
    • NMR analysis of the precipitate showed its silane/TPP nature.
    • NMR analysis of the precipitate showed its silane/TPP nature.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.