메뉴 건너뛰기




Volumn 64, Issue 19, 1999, Pages 7040-7047

Cis and enantioselective synthesis of 2-oxazoline-4-carboxylates through Lewis acid-catalyzed formal [3 + 2] cycloaddition of 5-alkoxyoxazoles with aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

5 METHOXY 2 (2 METHOXYPHENYL)OXAZOLE; 5 METHOXY 2 (4 METHOXYPHENYL)OXAZOLE; ACETONITRILE; ALDEHYDE; BENZALDEHYDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033578803     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990525d     Document Type: Article
Times cited : (48)

References (34)
  • 1
    • 0001679962 scopus 로고
    • For a review of the syntheses of 2-oxazoline-4-carboxylates using isocyanoacetates and conversion to β-hydroxyamino acid, see: Matsumoto, K.; Moriya, T.; Suzuki, M. J. Synth. Org. Chem. Jpn. 1985, 43, 7664.
    • (1985) J. Synth. Org. Chem. Jpn. , vol.43 , pp. 7664
    • Matsumoto, K.1    Moriya, T.2    Suzuki, M.3
  • 8
    • 1542499011 scopus 로고
    • (b) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215; 1988, 29, 239.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 239
  • 15
    • 0028329208 scopus 로고
    • Gold(I)-catalyzed asymmetric aldol reaction of methy isocyanoacetate with penta-and tetrafluorobenzaldehydes showed cis selectivity (cis/trans = 63:37-62:38) with high enentioselectivity (86-90% ee): Soloshonok, V. A.; Hayashi, T. Tetrahedron Lett. 1994, 35, 2713.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2713
    • Soloshonok, V.A.1    Hayashi, T.2
  • 19
    • 0032546117 scopus 로고    scopus 로고
    • Part of the present work has been presented as a communication letter: Suga, H.; Ikai, K.; Ibata, T. Tetrahedron Lett. 1998, 39, 869.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 869
    • Suga, H.1    Ikai, K.2    Ibata, T.3
  • 20
    • 0345491624 scopus 로고    scopus 로고
    • note
    • 3Al/(R)-BINOL = 1:1.05), the reaction (5 °C, 45 h) did not complete (61% yield, recovered 1b: 31%) and showed low selectivity (cis/trans = 79:21, cis: 63% ee).
  • 25
    • 0345491623 scopus 로고    scopus 로고
    • note
    • This may be attributable to the concomitant formation of minor trans-oxazolines by Lewis acid-promoted isomerization of cis-oxazolines through a ring-opening-recyclization pathway involving racemization of the 4-and 5-positions.
  • 26
    • 0001583380 scopus 로고
    • 18D = -50.2 ± 2° (c 2.0, 6 N HCl). Vogler, K. Helv. Chim. Acta 1950, 33, 2111.
    • (1950) Helv. Chim. Acta , vol.33 , pp. 2111
    • Vogler, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.