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Volumn , Issue 11, 2009, Pages 1886-1896

Application of phenolate ion mediated intramolecular epoxide ring opening in the enantioselective synthesis of functionalized 2,3-dihydrobenzofurans and 1-benzopyrans

Author keywords

2 hydroxymethyl chromans; 2 isopropenyl 2,3 dihydrobenzofuran; Epoxidation; Epoxides; Polycycles; Ring opening

Indexed keywords

2-HYDROXYMETHYL CHROMANS; 2-ISOPROPENYL-2,3-DIHYDROBENZOFURAN; EPOXIDES; POLYCYCLES; RING OPENING;

EID: 67650070300     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088077     Document Type: Article
Times cited : (18)

References (64)
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    • 67650044548 scopus 로고    scopus 로고
    • CDRI communication number 7184.
    • CDRI communication number 7184.
  • 6
    • 18844410273 scopus 로고    scopus 로고
    • For selected recent examples of 1-benzopyran-containing natural and unnatural molecules, see: a
    • For selected recent examples of 1-benzopyran-containing natural and unnatural molecules, see: (a) Wang, Y.; Mo, S.-Y.; Wang, S.-J.; Li, S.; Yang, Y.-C.; Shi, J.-G. Org. Lett. 2005, 7, 1675.
    • (2005) Org. Lett , vol.7 , pp. 1675
    • Wang, Y.1    Mo, S.-Y.2    Wang, S.-J.3    Li, S.4    Yang, Y.-C.5    Shi, J.-G.6
  • 16
    • 0042709607 scopus 로고    scopus 로고
    • For recent examples of enantioselective synthesis of 1-benzopyrans, see: a
    • For recent examples of enantioselective synthesis of 1-benzopyrans, see: (a) Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J.-P. J. Am. Chem. Soc. 2003, 125, 9276.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 9276
    • Trost, B.M.1    Shen, H.C.2    Dong, L.3    Surivet, J.-P.4
  • 45
    • 67650050677 scopus 로고    scopus 로고
    • US Patent 264947, 321133
    • Stack, G. P.; Gross, J. L. US Patent 264947, 2004; Chem. Abstr. 2003, 138, 321133.
    • (2003) Chem. Abstr , vol.138
    • Stack, G.P.1    Gross, J.L.2
  • 55
    • 67650015791 scopus 로고    scopus 로고
    • The enantiomeric excess values were determined by converting the epoxy alcohols into their Mosher ester derivatives and analyzing the 1H NMR spectra of the corresponding Mosher esters
    • 1H NMR spectra of the corresponding Mosher esters.
  • 56
    • 67650006426 scopus 로고    scopus 로고
    • In the tosylation reaction of 24a,b, formation of minor amount of the corresponding ditosylated products was also observed and these undesired products were eliminated by column chromatography
    • In the tosylation reaction of 24a,b, formation of minor amount of the corresponding ditosylated products was also observed and these undesired products were eliminated by column chromatography.
  • 57
    • 67650018829 scopus 로고    scopus 로고
    • The enantiomeric excess values of 27a,b were determined by chiral HPLC analysis.
    • The enantiomeric excess values of 27a,b were determined by chiral HPLC analysis.
  • 61
    • 67650056190 scopus 로고    scopus 로고
    • The enantiomeric excess values of 38a,b were determined by chiral HPLC analysis (Chiral Cel OD, petroleum ether (bp 30-60°C)-i-PrOH (98:2) 1 mL/min, 254 mm.
    • The enantiomeric excess values of 38a,b were determined by chiral HPLC analysis (Chiral Cel OD, petroleum ether (bp 30-60°C)-i-PrOH (98:2) 1 mL/min, 254 mm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.