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Volumn 74, Issue 6, 2009, Pages 2571-2574

Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: Preparation of valuable nitrogenated compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLOXYCARBONYL; CHEMOENZYMATIC ROUTES; ENZYMATIC DESYMMETRIZATION; MILD REACTION CONDITIONS; OPTICALLY ACTIVES; PSEUDOMONAS CEPACIA;

EID: 64149122933     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8025912     Document Type: Article
Times cited : (32)

References (31)
  • 10
    • 64149106155 scopus 로고    scopus 로고
    • Lemaire, M, Mangeney, P, Eds, Springer-Verlag: Berlin, Germany
    • Lemaire, M., Mangeney, P., Eds. Chiral Diazaligands for Asymmetric Synthesis; Springer-Verlag: Berlin, Germany, 2005.
    • (2005) Chiral Diazaligands for Asymmetric Synthesis
  • 11
    • 84891006345 scopus 로고    scopus 로고
    • For recent monographies on the topic, see: (a) Gotor, V, Alfonso, I, Garcia-Urdiales, E, Eds, Wiley: Weinheim, Germany
    • For recent monographies on the topic, see: (a) Gotor, V., Alfonso, I., Garcia-Urdiales, E., Eds. Asymmetric Organic Synthesis with Enzymes; Wiley: Weinheim, Germany, 2008.
    • (2008) Asymmetric Organic Synthesis with Enzymes
  • 13
    • 0003610122 scopus 로고    scopus 로고
    • Bornscheuer, U. T, Kazlauskas, R. J, Eds, Wiley: Weinheim, Germany
    • (c) Bornscheuer, U. T., Kazlauskas, R. J., Eds. Hydrolases in Organic Synthesis; Wiley: Weinheim, Germany, 2006.
    • (2006) Hydrolases in Organic Synthesis
  • 15
    • 33646473069 scopus 로고    scopus 로고
    • Gates, B. C, Knözinger, K, Eds, Elsevier: San Diego, Chapter 1, pp
    • (b) Reetz, M. T. In Advances in Catalysis, Vol. 49; Gates, B. C., Knözinger, K., Eds.; Elsevier: San Diego, 2006.; Chapter 1, pp 1-69.
    • (2006) Advances in Catalysis , vol.49 , pp. 1-69
    • Reetz, M.T.1
  • 26
    • 64149115755 scopus 로고    scopus 로고
    • Diol 5a was commercially available.
    • Diol 5a was commercially available.
  • 27
    • 64149089777 scopus 로고    scopus 로고
    • In all cases, diamines 8e-j were isolated with yields up to 75% except for compound 8e 54, In this case, elimination byproducts were detected in the reaction crude of die nucleophilic substitution with sodium azide
    • In all cases, diamines 8e-j were isolated with yields up to 75% except for compound 8e (54%). In this case, elimination byproducts were detected in the reaction crude of die nucleophilic substitution with sodium azide.
  • 28
    • 64149116270 scopus 로고    scopus 로고
    • Monoacetylation of compound 8h was also attempted, but we were not able to separate the enantiomers of the final product under any chiral HPLC conditions, so we decided to prepare 12h using benzoic anhydride instead of acetic anhydride.
    • Monoacetylation of compound 8h was also attempted, but we were not able to separate the enantiomers of the final product under any chiral HPLC conditions, so we decided to prepare 12h using benzoic anhydride instead of acetic anhydride.
  • 31
    • 64149083880 scopus 로고    scopus 로고
    • 3) for 70% ee found in our experimental conditions that has been obtained from (R)-10m.
    • 3) for 70% ee found in our experimental conditions that has been obtained from (R)-10m.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.