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Tetrahedron: Asymmetry
Volumn 5, Issue 7, 1994, Pages 1225-1228
Chemo-enzymatic approach to the synthesis of each of the four isomers of α-alkyl-β-fluoroalkyl-substituted β-amino acids
Author keywords

[No Author keywords available]
Indexed keywords

ALANINE DERIVATIVE; ALPHA ALKYL BETA FLUOROALKYL BETA ALANINE; UNCLASSIFIED DRUG;
EID: 0028023232     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/0957-4166(94)80163-0     Document Type: Article
Times cited : (87)
References (23)
  • 8
    • 0026005864 scopus 로고
    • To our knowledge only one type of fluorine-containing α-β-disubstituted β-amino acids namely, α-monofluorosubstituted ones are potentially available in optically pyre form by Welch chemistry
    • (1991) Tetrahedron Lett. , vol.32 , pp. 5461
    • Araki1    Wichtowski2    Welch3
  • 14
    • 84911303044 scopus 로고    scopus 로고
    • Was prepared with 78% isolated yield by condensation of methyl trifluoroacetate with methyl propionate under the action of sodium hydride.
  • 15
    • 84911310258 scopus 로고    scopus 로고
    • Yield 64%. Much lower yield in the DBU-catalyzed isomerization can explained by partial decomposition of products 3a,b through dehydrofluorination under the action of such a strong base as DBU.
  • 16
    • 84911300280 scopus 로고    scopus 로고
    • *)−3b, 1.24 (d, J = 7.2 Hz, 3 H), 3.15 (m, 1 H), 3.71 (s, 3 H), 4.11 (qu, J = 7.2 Hz, 1 H), 7.40–7.81 (m, 5 H), 8.37 (s, 1 H).
  • 17
    • 84911327551 scopus 로고    scopus 로고
    • *)−4b, 1.13 (dq, J = 7.2 Hz, 1.2 Hz, 3 H), 2.62 (dq, J = 7.2 Hz, 5.1 Hz, 1 H), 4.17 (dq, J = 7.8 Hz, 5.1 Hz, 1 H).
  • 18
    • 84911301137 scopus 로고    scopus 로고
    • 3. Diffraction data were measured on an Enraf-Nonius CAD4 diffractometer (Mo-radiation). 1063 Unique reflections were considered and used in the analysis. The structure was solved by Patterson method. The final R factor was 0.039.
  • 19
    • 84911324518 scopus 로고    scopus 로고
    • *)−5b, 1.21 (dq, J = 7.2 Hz, 0.6 Hz, 3 H), 2.96 (dq, J = 7.2 Hz, 4.5 Hz, 1 H), 2.68 (d, J = 2.1 Hz, 2 H), 4.89 (m, 1 H), 7.33 (m, 5 H), 7.62 (m, 1H).
  • 21
    • 0003065770 scopus 로고
    • It was shown in numerous studies that the structure of the leaving group of the substrates minimally affects the rate constants of the penicillin acylase-catalyzed hydrolytic reactions.
    • (1964) Nature , vol.203 , pp. 519
    • Cole1
  • 23
    • 0017666203 scopus 로고
    • Thus, in the penicillin acylase-catalyzed hydrolysis of N-phenylacetyl derivative of α-methyl-β-alanine corresponding (S)-amino acid was released by the enzyme with only 7.2% of enantiomeric purity.
    • (1977) Experientia , vol.15 , pp. 1557
    • Rossi1    Lucente2    Romeo3

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.