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Volumn , Issue 16, 2008, Pages 2451-2454

A straightforward synthesis of enantiopure 2,6-disubstituted morpholines by a regioselective O-protection/activation protocol

Author keywords

Epoxides; Morpholines; Phase transfer catalysis; Regioselectivity; Ring opening

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; HYDROXYL GROUP; MORPHOLINE DERIVATIVE; NITROGEN;

EID: 54349121133     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078054     Document Type: Article
Times cited : (19)

References (33)
  • 16
    • 54349120908 scopus 로고
    • 7th ed, British Crop Protection Council: Alton
    • (a) Worthing, C. R. The Pesticide Manual, 7th ed.; British Crop Protection Council: Alton, 1983, 265, 550.
    • (1983) The Pesticide Manual , vol.265 , pp. 550
    • Worthing, C.R.1
  • 32
    • 54349089711 scopus 로고    scopus 로고
    • Synthesis of (2R,6R)-2-Phenoxymethyl-6-phenyl-4-(toluene-4-sulfonyl) morpholine (11d, Typical Cyclization (Step v, In a screw cap vial, a heterogeneous mixture of 10d (0.60 g, 1 mmol) and TEBA (23 mg, 0.1 mmol) solution in anhyd MeCN (10 mL, and anhyd Cs2CO3 (0.83 g, 2.5 mmol, was magnetically stirred at 25°C for 3 h. Then the crude was diluted with CH2Cl2 (10 mL, and filtered through a celite pad. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (230-400 mesh, EtOAc-hexane, 1:4) to give 11d (373 mg, 88, as a white solid; mp 146-148°C; ee >99, HPLC: 4.6/250 mm CHIRALPAK-AD column, 25°C, i-PrOH-hexane (75:25, flow 0.8 mL/min; tR, 11.9 min; [α]D20 -31.1 (c, 1.0, CHCl3, IRNujol, 1598, 1587, 1493, 1345, 1236, 1167, 1131, 1122, 1065, 1051, 968, 813, 776
    • 3): δ = 7.78 (d, 2 H, J = 8.3 Hz), 7.72 (d, 2 H, J = 8.2 Hz), 7.21-7.31 (m, 11 H), 6.93 (t, 1 H, J = 7.3 Hz), 6.66 (d, 2 H, J = 8.1 Hz), 5.00 (dd, 1 H, J = 8.5, 4.7 Hz), 4.82-4.87 (m, 1 H), 4.30-4.33 (m, 1 H), 4.07 (dd, 1 H, J = 11.0, 3.5 Hz), 3.99 (dd, 1 H, J = 11.0, 5.8 Hz)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.