메뉴 건너뛰기




Volumn 45, Issue 2, 2004, Pages 411-415

Studies on the intramolecular oxa-Pictet-Spengler rearrangement of 5-aryl-1,3-dioxolanes to 4-hydroxy-isochromans

Author keywords

Dioxolanes; Isochromans; Isomerization; Oxa Pictet Spengler; Rearrangement

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ISOCHROMAN DERIVATIVE; TITANIUM DIOXIDE;

EID: 0346365498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.143     Document Type: Article
Times cited : (42)

References (40)
  • 6
    • 0038293225 scopus 로고    scopus 로고
    • Cutler, H. G.; Majetich, G.; Tian, X.; Spearing, P. U.S. Patent 5,922,889, 1999; Chem. Abstr. 1999, 131, 73559 TenBrick R.E., Bergh C.L., Ducan J.N., Harris D.W., Huff R.M., Lathi R.A., Lawson C.F., Lutzke B.S., Martin I.J., Rees S.A., Schlachter S.K., Sih J.S., Smith M.W. J. Med. Chem. 39:1996;2435-2437 Fráter G., Kraft P. Helv. Chim. Acta. 82:1999;1656-1665.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 1656-1665
    • Fráter, G.1    Kraft, P.2
  • 29
    • 85030925829 scopus 로고    scopus 로고
    • note
    • 18b 192-195 °C) and 159-160 °C, respectively.
  • 32
    • 85030924201 scopus 로고    scopus 로고
    • note
    • 13C resonances was supported by DEPT experiments.
  • 33
    • 85030921991 scopus 로고    scopus 로고
    • note
    • 4Cl (5 mL), warmed to rt, and extracted with EtOAc (3 × 30 mL).
  • 36
    • 85030916229 scopus 로고    scopus 로고
    • note
    • 3): δ 1.77 (bs, 1H), 1.98-2.14 (m, 1H), 2.20-2. 43 (m, 1H), 2.82-2.92 (m, 1H), 3.32 (ddd, J=3.1 , 12.1, 12.5 Hz, 1H), 4.80 (bt, 1H), and 7.02-7.35 (m, 4 H).
  • 37
    • 85030923418 scopus 로고    scopus 로고
    • note
    • ′- methoxyphenyl)-2,5-dimethyl-1,3-dioxolane gave less than 20% of rel-(1S,3S,4S)-1,3-dimethyl-4-hydroxy-6-methoxy-isochroman.
  • 38
    • 0000575831 scopus 로고    scopus 로고
    • Chemical shift changes have been observed in other titanium complexes. See, for example: (a) Singh D.K., Springer J.B., Goodson P.A., Corcoran R.C. J. Org. Chem. 61:1996;1436-1442 (b) Corcoran R.C., Ma J. J. Am. Chem. Soc. 114:1992;4536-4542.
    • (1996) J. Org. Chem. , vol.61 , pp. 1436-1442
    • Singh, D.K.1    Springer, J.B.2    Goodson, P.A.3    Corcoran, R.C.4
  • 39
    • 0000545078 scopus 로고
    • Chemical shift changes have been observed in other titanium complexes. See, for example: (a) Singh D.K., Springer J.B., Goodson P.A., Corcoran R.C. J. Org. Chem. 61:1996;1436-1442 (b) Corcoran R.C., Ma J. J. Am. Chem. Soc. 114:1992;4536-4542.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4536-4542
    • Corcoran, R.C.1    Ma, J.2
  • 40
    • 85030920308 scopus 로고    scopus 로고
    • 2CN (0.08)
    • 2CN (0.08).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.