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Volumn 12, Issue 17, 2010, Pages 3772-3775

Resolution of 2,2-disubstituted epoxides via biocatalytic azidolysis

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; AZIRIDINE DERIVATIVE; EPOXIDE; HALOHYDRIN DEHALOGENASE; HYDROLASE; SODIUM AZIDE;

EID: 77956222610     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101406k     Document Type: Article
Times cited : (58)

References (88)
  • 23
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    • For examples of selective reactions with 2-alkyl-2-aryl epoxides, see: Hydrolysis
    • For examples of selective reactions with 2-alkyl-2-aryl epoxides, see: Hydrolysis
  • 28
    • 77956201427 scopus 로고    scopus 로고
    • note
    • Codex Halohydrin dehalogenase enzymes were purchased from CODEXIS, Inc. (Redwood City, CA).
  • 29
    • 77956214286 scopus 로고    scopus 로고
    • For halohydrin dehalogenase reaction mechanisms, see
    • For halohydrin dehalogenase reaction mechanisms, see
  • 33
    • 77956224009 scopus 로고    scopus 로고
    • note
    • All of the 2,2-disubstituted epoxides (except for 2-methyl-2- phenyloxirane) needed for this study were prepared in >85% yield using the Corey-Chaykovsky epoxidation methodology
  • 36
    • 77956202978 scopus 로고    scopus 로고
    • note
    • For a complete description of all of the HHDH variants used in the Codex HHDH panel, see: ref 8b.
  • 37
    • 77956194840 scopus 로고    scopus 로고
    • note
    • 3) which had no influence on the azidolysis: see ref 5a.
  • 38
    • 77956210693 scopus 로고    scopus 로고
    • note
    • -3 mol % of enzyme.
  • 39
    • 77956206145 scopus 로고    scopus 로고
    • note
    • R(minor) 6.37 min (98% ee). SFC (supercritical fluid chromatography) where mobile phases are carbon dioxide and a polar modifier, methanol.
  • 40
    • 77956215142 scopus 로고    scopus 로고
    • note
    • 3, a major byproduct for this particular substrate was hydolysis of the epoxide providing the corresponding diol.
  • 41
    • 77956216091 scopus 로고    scopus 로고
    • note
    • In ref 6b, 90% ee was observed for this substrate.
  • 51
    • 77956219609 scopus 로고    scopus 로고
    • See the experimental details in the Supporting Information
    • See the experimental details in the Supporting Information.
  • 52
    • 77956213944 scopus 로고    scopus 로고
    • For studies on catalytic asymmetric aziridination reactions, see
    • For studies on catalytic asymmetric aziridination reactions, see
  • 72
    • 77956212294 scopus 로고    scopus 로고
    • For the synthesis of enantiomerically enriched amino alcohols, see
    • For the synthesis of enantiomerically enriched amino alcohols, see
  • 74
    • 77956214120 scopus 로고    scopus 로고
    • Reference 6a
    • Reference 6a.
  • 75
    • 77956214448 scopus 로고    scopus 로고
    • World Patent WO 9523869, 1995; US Patent 5,731,175, 1998; US Patent 5,846,792, 1998; US Patent 5,874,613
    • Nikaido, T.; Kawada, N.; Hamatani, T.; Ueda, Y. (Daicel Chemical Industries), World Patent WO 9523869, 1995; US Patent 5,731,175, 1998; US Patent 5,846,792, 1998; US Patent 5,874,613, 1999.
    • (1999) Daicel Chemical Industries
    • Nikaido, T.1    Kawada, N.2    Hamatani, T.3    Ueda, Y.4
  • 77
    • 77956217131 scopus 로고    scopus 로고
    • (Daicel Chemical Industries), Japanese Patent JP 46076
    • Ito, S.; Nikaido, T.; Matsuyama, A. (Daicel Chemical Industries), Japanese Patent JP 46076, 2001.
    • (2001)
    • Ito, S.1    Nikaido, T.2    Matsuyama, A.3
  • 79
    • 0036371962 scopus 로고    scopus 로고
    • references cited therein
    • Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1 and references cited therein
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 1
    • Trost, B.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.