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Volumn , Issue 18, 2008, Pages 2856-2858

Exploring substrate scope of Shi-type epoxidations

Author keywords

Alkenes; Asymmetric catalysis; Epoxidations; Ligands; Organocatalysis

Indexed keywords

ALKENE; CARBOHYDRATE; SODIUM PEROXIDE; STYRENE DERIVATIVE;

EID: 56849112281     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083545     Document Type: Article
Times cited : (13)

References (29)
  • 1
    • 0000345527 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Heidelberg
    • (a) Katsuki, T. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 621-648.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 621-648
    • Katsuki, T.1
  • 2
    • 0000635013 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Heidelberg
    • (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 649-677.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 649-677
    • Jacobsen, E.N.1    Wu, M.H.2
  • 4
    • 0003544583 scopus 로고    scopus 로고
    • 2nd ed, Ojima, I, Ed, Wiley-VCH: New York
    • (d) Katsuki, T. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 287-325.
    • (2000) Catalytic Asymmetric Synthesis , pp. 287-325
    • Katsuki, T.1
  • 8
    • 0034536438 scopus 로고    scopus 로고
    • For leading references on this transformation, see: a
    • For leading references on this transformation, see: (a) Frohn, M.; Shi, Y. Synthesis 2000, 1979.
    • (2000) Synthesis , pp. 1979
    • Frohn, M.1    Shi, Y.2
  • 16
    • 56849085860 scopus 로고    scopus 로고
    • Diacetate 2 is a very effective as epoxidation catalyst using 10 mol% of catalyst loading. Loading for Shi's catalysts usually ranges from 20 mol% to 30 mol%. See refs. 4a-c.
    • Diacetate 2 is a very effective as epoxidation catalyst using 10 mol% of catalyst loading. Loading for Shi's catalysts usually ranges from 20 mol% to 30 mol%. See refs. 4a-c.
  • 19
    • 56849126961 scopus 로고    scopus 로고
    • Compound 4e (0.37 g, 46% yield) was obtained as a colourless oil. 1H NMR (400 MHz, CDCl3, δ, 7.27-7.40 (m, 15 H, 6.48 (dt, 1 H, J, 16.0, 1.3 Hz, 6.28 (dt, 1 H, J, 16.0, 6.9 Hz, 5.42 (s, 1 H, 3.62 (t, 2 H, J, 6.9 Hz, 2.60 (qd, 2 H, J, 6.9, 1.3 Hz, 13CNMR: δ, 142.4, 137.7, 131.6, 128.5, 128.4, 127.4, 127.3, 127.2, 127.0, 126.0, 83.7, 68.7, 33.6. The asymmetric epoxidation of alkene 4e to give, )-5e was carried out by the general procedure (see ref. 12, Compound 5e (0.15 g, 52% yield, white solid; mp 56°C; [α]D25 +28.53 (c 0.12, CH 2Cl2, IR: 2871-3066, 1599, 1491, 1097, 1037, 855 cm -1. 1H NMR (400 MHz, CDCl3, δ, 7.12-7.36 (m, 15 H, 5.36 (s, 1 H, 3.69 (d, 1 H, J, 1.9 Hz, 3.65 (t, 2 H, J, 6.0 Hz, 3.13 (td, J, 5.6, 1.9 Hz, 2.02 td, 2 H, J
    • R (minor) =11.7 min.
  • 20
    • 56849124751 scopus 로고    scopus 로고
    • General Procedure for the Epoxidation of Alkenes: The corresponding alkene (2.22 mmol) and the required amount of catalyst 3 (10-30 mol, were dissolved in MeCN-dimethoxymethane (44 mL, 1:2, A pH 6 buffer solution (8 mL, tetrabutylammonium hydrogen sulfate (35 mg, 0.10 mmol) was slowly added with stirring and the mixture was cooled to the desired temperature. The flask was equipped with two syringe pumps; one of them was filled with a solution of Oxone (3.62-6.82 mmol) in pH 6 buffer (14 mL) and the other one with a solution of K2CO3 (5.33-16.06 mmol) in H2O (14 mL, The two solutions were added dropwise over a 2 h period (syringe pump, The solution was stirred at 0°C for the corresponding reaction time. The mixture was diluted with H2O (40 mL) and extracted with the appropriate organic solvent [5a and 5h: hexane (4 x 40 mL, 5b-g,i-l: CH2Cl2 4 x 40 mL, The combined organic fr
    • 21 HPLC: Chiralcel AD-H. For 51 GC: gamma dex.
  • 21
    • 0028273577 scopus 로고
    • Higher pH values were not considered since the background reaction could be significant. See
    • Higher pH values were not considered since the background reaction could be significant. See: Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577.
    • (1994) Tetrahedron Lett , vol.35 , pp. 1577
    • Kurihara, M.1    Ito, S.2    Tsutsumi, N.3    Miyata, N.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.