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Volumn 9, Issue 2, 2007, Pages 215-218

Highly efficient synthesis of enantiomerically enriched 2-hydroxymethylaziridines by enzymatic desymmetrization

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

EID: 33846615885     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062643a     Document Type: Article
Times cited : (27)

References (25)
  • 1
    • 0036374173 scopus 로고    scopus 로고
    • For reviews on the synthesis and reactions of chiral aziridines, see: a
    • For reviews on the synthesis and reactions of chiral aziridines, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
    • (2002) Chem. Soc. Rev , vol.31 , pp. 247
    • Sweeney, J.B.1
  • 5
    • 0042881024 scopus 로고    scopus 로고
    • and references cited therein
    • (d) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905 and references cited therein.
    • (2003) Chem. Rev , vol.103 , pp. 2905
    • Müller, P.1    Fruit, C.2
  • 8
    • 0030590954 scopus 로고    scopus 로고
    • A few direct aziridinations of styrene have been reported: (a) Nishikori, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245.
    • A few direct aziridinations of styrene have been reported: (a) Nishikori, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245.
  • 11
    • 0037150595 scopus 로고    scopus 로고
    • Asymmetirc synthesis of 2-hydroxymethylazirine has been briefly reported from chiral amino acid without isolation and characterization: Xu, J. Tetrahedron: Asymmetry 2002, 13, 1129.
    • Asymmetirc synthesis of 2-hydroxymethylazirine has been briefly reported from chiral amino acid without isolation and characterization: Xu, J. Tetrahedron: Asymmetry 2002, 13, 1129.
  • 16
    • 13344277260 scopus 로고    scopus 로고
    • For a review of enantioselective enzymatic desymmetrizations in organic synthesis, see
    • For a review of enantioselective enzymatic desymmetrizations in organic synthesis, see: Garcia-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313.
    • (2005) Chem. Rev , vol.105 , pp. 313
    • Garcia-Urdiales, E.1    Alfonso, I.2    Gotor, V.3
  • 20
    • 0034608087 scopus 로고    scopus 로고
    • For a review of enhancement of selectivity and reactivity of lipase by additives, see
    • For a review of enhancement of selectivity and reactivity of lipase by additives, see: Theil, F. Tetrahedron 2000, 56, 2905.
    • (2000) Tetrahedron , vol.56 , pp. 2905
    • Theil, F.1
  • 21
    • 33846591034 scopus 로고    scopus 로고
    • Free 2-hydroxymethylaziridine 6 was dimerized or oligomerized under acidic conditions or at temperature higher than ca. 50°C. Therefore, it was purified by chromatography on basic alumina.
    • Free 2-hydroxymethylaziridine 6 was dimerized or oligomerized under acidic conditions or at temperature higher than ca. 50°C. Therefore, it was purified by chromatography on basic alumina.
  • 24
    • 33846644515 scopus 로고    scopus 로고
    • 3N. Benzyl alcohol was rapidly produced at -10°C, which is a byproduct from Cbz deprotection.
    • 3N. Benzyl alcohol was rapidly produced at -10°C, which is a byproduct from Cbz deprotection.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.