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Volumn , Issue 4, 2007, Pages 646-648

Ytterbium(III) triflate catalyzed [3+2] cycloaddition of N-arylimines and epoxides: A novel and solvent-free synthesis of substituted 1,3-oxazolidines

Author keywords

1,3 oxazolidines; Cycloaddition; Epoxides; N arylimines; Ytterbium(III) triflate

Indexed keywords

5 CHLOROMETHYL 2,2 DIPHENYL 3 4 TOLYLOXAZOLIDINE; 5 CHLOROMETHYL 2,3 DIPHENYLOXAZOLIDINE; EPOXIDE; IMINE; OXAZOLIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; YTTERBIUM;

EID: 33947235817     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967975     Document Type: Article
Times cited : (29)

References (27)
  • 18
    • 33947222672 scopus 로고    scopus 로고
    • 5-Chloromethyl-2,3-diphenyloxazolidine (3a, MS (EI, m/z, 273 (100, 196 (84, 132 (67, IR (film, 1297, 1207, 1109 cm -1; 1H NMR (400 MHz, CDCl3, δ (cis-3a, 7.48-7.36 (m, 5 H, 7.16 (t, J, 7.6 Hz, 2 H, 6.75 (t, J =7.6 Hz, 1 H, 6.52 (d, J, 7.6 Hz, 2 H, 5.87 (s, 1 H, 4.59-4.50 (m, 1 H, 3.96 (dd, J, 6.0, 8.4 Hz, 1 H, 3.85-3.59 (m, 2 H, 3.51 (dd, J, 8.4, 8.4Hz, 1 H, 13CNMR (100 MHz, CDCl 3-TMS, δ(cis-3a, 145.4, 139.3, 129.1, 128.9, 128.8, 127.1, 118.2, 113.9, 92.9, 76.7, 52.2, 44.6; 1H NMR (400 MHz, CDCl3, δ (trans-3a, 7.48-7.36 (m, 5 H, 7.16 (t, J, 7.6 Hz, 2 H, 6.75 (t, J, 7.6 Hz, 1 H, 6.52 (d, J, 7.6 Hz, 2 H, 6.01 (s, 1 H, 4.59-4.50 (m, 1 H, 3.98 (dd, J, 6.0, 8.4 Hz, 1 H, 3.85-3.59 (m, 2 H, 3.51 dd, J, 8.4, 8.4 Hz, 1 H, 13
    • 22ClNO: C, 75.92; H, 6.09; N, 3.85. Found: C, 75.90; H, 6.10; N, 3.84.
  • 20
    • 0035528735 scopus 로고    scopus 로고
    • It has been reported that in the 1H NMR data for the cis configuration of 3a and 3d, the proton in the 2-position appeared at δ, 5.85 and δ, 5.84 ppm, respectively; see: Bulatova, O. F, Chalova, O. B, Rakhmankulov, D. L, Chem. 2001, 37, 1753
    • 1H NMR data for the cis configuration of 3a and 3d, the proton in the 2-position appeared at δ = 5.85 and δ = 5.84 ppm, respectively; see: Bulatova, O. F.; Chalova, O. B.; Rakhmankulov, D. L. Russ. J. Org. Chem. 2001, 37, 1753.
  • 21
    • 33947210384 scopus 로고    scopus 로고
    • 3 (0.06 g, 5 mol%) was stirred at 40°C for 8 h. After complete conversion into 3a, as indicated by TLC, the reaction mixture was purified by silica gel column chromatography using PE-EtOAc (10:1) as eluent to afford the pure product 5-chloromethyl-2,3- diphenyloxazolidine (3a, 0.46 g, 85%, Table 2).
    • 3 (0.06 g, 5 mol%) was stirred at 40°C for 8 h. After complete conversion into 3a, as indicated by TLC, the reaction mixture was purified by silica gel column chromatography using PE-EtOAc (10:1) as eluent to afford the pure product 5-chloromethyl-2,3- diphenyloxazolidine (3a, 0.46 g, 85%, Table 2).
  • 23
    • 33947228500 scopus 로고    scopus 로고
    • HPLC conditions: Chiracel OD 4.6 x 250mm, hexane-i-PrOH (85:15), 25°C.
    • HPLC conditions: Chiracel OD 4.6 x 250mm, hexane-i-PrOH (85:15), 25°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.