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Synlett
Volumn , Issue 20, 2006, Pages 3521-3524
Organocatalytic asymmetric synthesis of 1,2,3-prim,sec,sec-triols
Author keywords

Asymmetric catalysis; Epoxidation; Epoxide opening; Tandem reactions; Triols
Indexed keywords

1,2,3 TRIOL DERIVATIVE; 3 CHLORO 1,2 PROPANDIOL DERIVATIVE; ALDEHYDE; EPOXIDE; HYDROGEN PEROXIDE; OXIDIZING AGENT; PROPYLENE GLYCOL; SIALIC ACID DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; ZANAMIVIR;
EID: 33846501571     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-956488     Document Type: Article
Times cited : (21)
References (53)
  • 7
    • 0000743188 scopus 로고
    • For example of diastereoselective methods, see: a
    • For example of diastereoselective methods, see: (a) Delton, M. H.; Yuen, G. U. J. Org. Chem. 1968, 33, 2473.
    • (1968) J. Org. Chem , vol.33 , pp. 2473
    • Delton, M.H.1    Yuen, G.U.2
  • 11
    • 0000509394 scopus 로고
    • For selected examples of enzyme-catalyzed methods, see: a
    • For selected examples of enzyme-catalyzed methods, see: (a) Effenberger, F.; Hopf, M.; Ziegler, T.; Hudelmayer, J. Chem. Ber. 1991, 124, 1651.
    • (1991) Chem. Ber , vol.124 , pp. 1651
    • Effenberger, F.1    Hopf, M.2    Ziegler, T.3    Hudelmayer, J.4
  • 22
  • 24
    • 84985609389 scopus 로고    scopus 로고
    • For examples of organocatalytic epoxidations, see: (a) Julia, S, Masana, J, Vega, J. C. Angew. Chem, Int. Ed. Engl. 1980, 19, 929
    • For examples of organocatalytic epoxidations, see: (a) Julia, S.; Masana, J.; Vega, J. C. Angew. Chem., Int. Ed. Engl. 1980, 19, 929.
  • 30
    • 4143088133 scopus 로고    scopus 로고
    • For the use of chiral ketones as catalysts, see:, and references therein
    • (g) For the use of chiral ketones as catalysts, see: Shi, Y. Acc. Chem. Res. 2004, 37, 488; and references therein.
    • (2004) Acc. Chem. Res , vol.37 , pp. 488
    • Shi, Y.1
  • 47
    • 14644408766 scopus 로고    scopus 로고
    • With other oxidants, see: Engqvist, M, Casas, J, Sundén, H, Ibrahem, I, Córdova, A. Tetrahedron Lett. 2005, 46, 2053
    • (m) With other oxidants, see: Engqvist, M.; Casas, J.; Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2005, 46, 2053.
  • 51
    • 33846543155 scopus 로고    scopus 로고
    • To a stirred solution of 3 (16 mg, 20 mol, in CHCl3 (2 mL) was added trans-cinnamaldehyde (1a, 66 mg, 0.5 mmol) and H 2O2 (0.6 mmol, 50% aq solution, The reaction was vigorously stirred at 4 °C for 7 h. Then the reaction mixture was diluted with EtOH (2 mL) and cooled to 0 °C followed by addition of NaBH4 (38 mg, 1.0 mmol, The mixture was then stirred for 10 min, quenched with H2SO4 (0.5 N, 8 mL) and EtOAc (8 mL, Next, the reaction mixture was stirred at r.t. for 1 h. The mixture was separated and the water layer was extracted with EtOAc (6 × 5 mL, The organic layer was collected, dried over Na2SO4 and the solvent was removed. The residue was purified by silica gel chromatography (EtOAc) to give the product 2a (53 mg, 63, 2R,3S)-1-Phenyl-propane-1,2,3-triol (2a, a]D25 +30.3 c 1.0, CHCl3, a]D25
    • +: 191.0679; found: 191.0687.
  • 52
    • 33846489573 scopus 로고    scopus 로고
    • To a stirred solution of 3 (16 mg, 20 mol, in CHCl3 (2 mL) was added trans-cinnamaldehyde (1a, 66 mg, 0.5 mmol) and H 2O2 (0.6 mmol, 50% aq solution, The reaction was vigorously stirred at 4 °C for 7 h. Then the reaction mixture was diluted with EtOH (2 mL) and cooled to 0 °C followed by addition of NaBH4 (38 mg, 1.0 mmol) and the mixture was stirred for 10 min. Next, NaOH (0.5 N, 10 mL) and t-BuOH (2 mL) were added and the reaction temperature increased to 70 °C. After 24 h of stirring at this temperature, the mixture was separated and the water layer was extracted with EtOAc (6 × 5 mL, Then the organic layer was collected, dried over Na2SO4 and the solvent was removed. The crude residue was purified by silica gel chromatography using a gradient system (pentane-EtOAc, 1:1) to give the 2-epoxy alcohol (45 mg) and then EtOAc to give the triol 2a 39 mg, 39
    • 4 and the solvent was removed. The crude residue was purified by silica gel chromatography using a gradient system (pentane-EtOAc = 1:1) to give the 2-epoxy alcohol (45 mg) and then EtOAc to give the triol 2a (39 mg, 39%).
  • 53
    • 33846544338 scopus 로고    scopus 로고
    • To a stirred solution of 3 (16 mg, 20 mol, in CHCl3 (2 mL) was added trans-cinnamaldehyde (1a, 66 mg, 0.5 mmol) and H 2O2 (0.6 mmol, 50% aq solution, The reaction was vigorously stirred at 4 °C for 7 h. Then the reaction mixture was diluted with EtOH (2 mL) and cooled to 0 °C followed by addition of NaBH4 (38 mg, 1.0 mmol) After 10 min of stirring, EtOAc (8 mL) and HCl (2 N, 4 mL) were added. The mixture was extracted and the water layer was extracted with EtOAc (3 × 5 mL, The organic layers were collected, dried over Na 2SO4 and the solvent was removed. The residue was purified by silica gel chromatography (pentane-EtOAc, 1:1) to give 4b (68, Compound 4b: [a]D25 +25.7 (c 1.0, CHCl 3, 1H NMR (400 MHz, CDCl3, d, 3.78 (dd, J, 6.4, 12.8 Hz, 1 H, 3.85 (dd, J, 3.2, 12.8 Hz, 1 H, 4.01-4.04 (m, 1 H, 4.84 d, J, 7.6 Hz
    • +: 242.9950; found: 242.9952.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.