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Volumn 49, Issue 6, 2008, Pages 977-979

Practical chemoenzymatic dynamic kinetic resolution of primary amines via transfer of a readily removable benzyloxycarbonyl group

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLBENZYLAMINE; AMINE; BENZYL CARBAMATE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; DIBENZYL CARBONATE; RUTHENIUM; UNCLASSIFIED DRUG;

EID: 37849035610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.017     Document Type: Article
Times cited : (65)

References (22)
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    • Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • Blaser H.U., and Spindler F. Hydrogenation of Imino Groups. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 1 (1999), Springer, Berlin 247-265
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 247-265
    • Blaser, H.U.1    Spindler, F.2
  • 3
    • 0003779363 scopus 로고    scopus 로고
    • The Reduction of Imines and Enamines with Transition Metal Hydrides
    • Beller M., and Bolm B. (Eds), Wiley-VCH, Weinheim
    • Singaram B., and Goralski C.T. The Reduction of Imines and Enamines with Transition Metal Hydrides. In: Beller M., and Bolm B. (Eds). Transition Metals for Organic Synthesis Vol. 2 (1998), Wiley-VCH, Weinheim 147-154
    • (1998) Transition Metals for Organic Synthesis , vol.2 , pp. 147-154
    • Singaram, B.1    Goralski, C.T.2
  • 4
    • 0001059120 scopus 로고    scopus 로고
    • Alkylation of Imino Groups
    • Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • Denmark S.E., and Nicaise O.J.C. Alkylation of Imino Groups. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Berlin 923-961
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 923-961
    • Denmark, S.E.1    Nicaise, O.J.C.2
  • 5
    • 0000189702 scopus 로고    scopus 로고
    • Recent Advances in Asymmetric Dihydroxylation and Aminohydroxylation
    • Ojima I. (Ed), Wiley-VCH, New York
    • Bolm C., Hildebrand J.P., and Muniz K. Recent Advances in Asymmetric Dihydroxylation and Aminohydroxylation. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, New York 399-428
    • (2000) Catalytic Asymmetric Synthesis. 2nd ed. , pp. 399-428
    • Bolm, C.1    Hildebrand, J.P.2    Muniz, K.3
  • 7
    • 37849040845 scopus 로고    scopus 로고
    • Martín-Matute, B.; Bäckvall, J. E. Chemoenzymatic Deracemization Processes. In Organic Synthesis with Enzymes in Nonaqueous Solvents, Riva S. Ed., Wiley-VCH, in press.
  • 16
    • 34347354229 scopus 로고    scopus 로고
    • For related work on ruthenium- and enzyme-catalyzed DKR of alcohols see:
    • For related work on ruthenium- and enzyme-catalyzed DKR of alcohols see:. Bogár K., and Bäckvall J.E. Tetrahedron Lett. 48 (2007) 5471-5474
    • (2007) Tetrahedron Lett. , vol.48 , pp. 5471-5474
    • Bogár, K.1    Bäckvall, J.E.2
  • 19
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    • note
    • For example, acidic hydrolysis of the acetamide of 1-phenylethylamine requires reaction at 140 °C for 48 h in concentrated hydrochloric acid.
  • 20
    • 37849050790 scopus 로고    scopus 로고
    • note
    • The racemization with catalyst 1 under the DKR conditions requires a temperature of 90 °C (see Ref. 6).
  • 22
    • 37849013640 scopus 로고    scopus 로고
    • note
    • It is not clear why the allyl carbonate gives only a moderate enantioselectivity since there was no background reaction in the control reaction. A likely explanation is that the enzyme itself has some effect on the non-catalyzed reaction, increasing the reaction pathway via direct acylation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.