Stereoselective synthesis of 2-(S)-(3,5-bis(trifluoromethyl) benzyloxy)-3-(S)-phenyl-1,4-oxazine

Tetrahedron Asymmetry

Volumn 8, Issue 6, 1997, Pages 957-963

  Ashwood, Michael S ^a   Cottrell, Ian F ^a   Davies, Antony J ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 OXAZINE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0030987107     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00058-X     Document Type: Article

References (15)

1. Hale, J. J. et al. J. Med. Chem. 1996, 39, 1760-1762.
2. Kashima, C; Harada, K. J. Chem. Soc. Perkin Trans. I 1988, 1521-1526.
3. Jankowski, K.; Berse, C. Can. J. Chem. 1968, 46, 1939-1942.
4. Chang, C.-J.; Fang, J.-M.; Lee, G.-H.; Wang, Y. J. Chem. Soc. Perkin Trans, I 1994, 3587-3593.
5. Agami, C.; Couty, F.; Prince, B.; Puchot, C. Tetrahedron 1991, 47 (25), 4343-4354.
6. Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen. D. J Am. Chem. Soc. 1988, 110, 1547-1557.
7. Gerlach, H. Helv. Chim. Acta 1966, 49, 2481-2489.
8. HPLC System: 250 × 4.6 mm covalently bonded D-phenylglycine, 4% isopropanol 96% hexane, 210 nm, 1.0 ml/min. Retention times: R-enantiomer 28.0 min, S-enantiomer 29.3 min
9. 2 (HC1 salt): C, 53.08; H, 4.98; Cl, 9.22; Br, 20.77; N, 3.64. Found: C, 53.13; H, 5.05; Cl, 8.95; Br, 20.71; N, 3.65.
10. Stang, P. J; Treptow, W. Synthesis 1980, 283.
11. 2) of the triflate 4 gave the following δ (ppm) for the benzylic protons: 5.54 triflate 4 (singlet) 5.34 alcohol 9 (doublet, J=5.1 Hz) 4.68 ether 11 (singlet)
12. Other reducing agents such as Dibal-H or Red-Al were effective in reducing the oxazinone 3 but the resulting alkoxide did not alkylate with the triflate.
13. Brown, H. C.; Krishnamurthy, S. J. Org. Chem. 1972, 94, 7159-7161.
14. 3CN, 1.5 mL/min, 220 nm. Time/min %A %B 0 60 40 20 10 90 30 10 90 Retention times: (2S,3S;5) 24.76 min, (2R,3S; 12) 25.12 min, (2S,3S; 6) 15.88 min, (2R,3S; 13) 16.53 min.
15. 3CN, 1.5 mL/min, 220 nm. Retention times: (2S,3S; 6) 15.8 min, (2R,3R) 17.4 min.