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Synlett
Volumn , Issue 20, 2007, Pages 3198-3200
Dimethyldioxirane oxidation of 2-silyloxypyrroles: An efficient regiocontrolled synthesis of 5-hydroxy-3-pyrrolin-2-ones
Author keywords

Alkaloids; Lactams; Oxyfunctionalization; Regioselectivity; Wittig reaction
Indexed keywords

2 SILYLOXYPYRROLE DERIVATIVE; 2 TRIISOPROPYLSILYLOXYPYRROLE DERIVATIVE; 5 HYDROXY 3 PYRROLIN 2 ONE DERIVATIVE; DIMETHYLDIOXIRANE; N TERT BUTYLOXYCARBONYL 3 PYRROLIN 2 ONE DERIVATIVE; N TERT BUTYLOXYCARBONYL 5 HYDROXY 3 PYRROLIN 2 ONE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 37749021705     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992376     Document Type: Article
Times cited : (13)
References (48)
  • 29
    • 37749013095 scopus 로고    scopus 로고
    • For the vinylogous oxyfunctionalization of 2-silyloxyfurans with DMDO, see: (a) Boukouvalas, J.; Lachance, N. Synlett 1998, 31.
    • For the vinylogous oxyfunctionalization of 2-silyloxyfurans with DMDO, see: (a) Boukouvalas, J.; Lachance, N. Synlett 1998, 31.
  • 40
    • 37749039640 scopus 로고    scopus 로고
    • Typical Procedure: To a solution of 4a (732 mg, 4.0 mmol) in anhyd CH2Cl2 (5 mL) were added 2,6-lutidine (1.290 g, 12.0 mmol) and TIPSOTf (1.232 g, 4.54 mmol) under nitrogen at r.t. After stirring for 30 min, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (hexanes-EtOAc, 95:5) to give 5a (1.263 g, 93, as a colorless oil. For smaller-scale reactions, purification was carried out by chromatography on basic silica gel.11c Data for 5a: 1H NMR (300 MHz, CDCl3, δ, 1.10 (d, J, 7.2 Hz, 18 H, 1.25 (hept, J, 7.2 Hz, 3 H, 1.54 (s, 9 H, 5.21 (dd, J, 1.7, 3.6 Hz, 1 H, 5.86 (dd, J, 1.7, 3.6 Hz, 1 H, 6.67 (t, J, 3.6 Hz, 1 H, 13C NMR 75 MHz, CDCl3, δ, 12.4, 17.9, 27.8, 82.4, 91.7, 107.6, 112.5, 143.6, 148.1. HRMS: m/z calcd for C18H33NO3Si: 339.2230;
    • 3Si: 339.2230; found: 339.2233.
  • 43
    • 37749019190 scopus 로고    scopus 로고
    • Typical Procedure: To a solution of 5a (339 mg, 1.0 mmol) in anhyd CH2Cl2 (5 mL) at -78°C was added dropwise a solution of DMDO (0.055 M in acetone, 20 mL, 1.1 equiv) and the reaction mixture was stirred for 1 h at -78°C The volatiles were evaporated and the residue was dissolved in acetone (10 mL, After addition of H2O (7 mL) and Amberlyst-15 (ca. 100 mg, the reaction mixture was stirred for 1 h at r.t. The mixture was filtered, the filtrate was extracted with Et2O (3 x 10 mL) and the combined organic layers were dried over anhyd MgSO4. After evaporation of the volatiles, the residue was purified by flash chromatography on silica gel (hexanes-EtOAc, 7:3) to furnish 6a (187 mg, 94, as a white solid (mp 100-101°C, 1H NMR (300 MHz, CDCl 3, δ, 1.54 (s, 9 H, 4.32 (br d, J, 4.8 Hz, 1 H, 5.96 (br m, 1 H, 6.07 (d, J, 6.4 Hz, 1 H, 7.02 dd, J, 4
    • 4: C, 54.26; H, 6.58; N, 7.03. Found: C, 54.62; H, 6.53; N, 7.00.
  • 44
    • 84951531840 scopus 로고    scopus 로고
    • Epoxides have been obtained from reactions of DMDO with indoles: Zhang, X.; Foote, C S. J. Am. Chem. Soc. 1993, 115, 8867.
    • Epoxides have been obtained from reactions of DMDO with indoles: Zhang, X.; Foote, C S. J. Am. Chem. Soc. 1993, 115, 8867.
  • 45
    • 37749020123 scopus 로고    scopus 로고
    • 4: C, 62.90; H, 7.92; N, 5.24. Found: C, 62.84; H, 7.87; N, 5.16.
    • 4: C, 62.90; H, 7.92; N, 5.24. Found: C, 62.84; H, 7.87; N, 5.16.
  • 46
    • 37749012170 scopus 로고    scopus 로고
    • For the removal of the Boc group from compounds 6b,c using neat TFA at 0°C, see: Yakushijin, K.; Suzuki, R.; Hattori, R.; Furukawa, H. Heterocycles 1981, 16, 1157.
    • For the removal of the Boc group from compounds 6b,c using neat TFA at 0°C, see: Yakushijin, K.; Suzuki, R.; Hattori, R.; Furukawa, H. Heterocycles 1981, 16, 1157.
  • 48
    • 37749034913 scopus 로고    scopus 로고
    • 5: 284.1498; found: 284.1502.
    • 5: 284.1498; found: 284.1502.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.