Asymmetric synthesis of (+)- and (-)-2-(2-methoxyphenyl)-3,1-benzoxathiane

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 1903-1906

  Bassoli, Angela ^a   Merlini, Lucio ^a   Baldoli, Clara ^b   Maiorana, Stefano ^b   Drew, Michael G B ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 OXATHIANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030200769     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00226-1     Document Type: Article

References (18)

1. 1. Lynch, J.E.; Eliel, E. L.; J. Am. Chem. Soc., 1984,106, 2943-2948.
2. 2. a) Solladié-Cavallo, A. in Adv. in Metal-Organic Chemistry, Liebeskind, L. S. Ed.; JA1: Greenwich, 1989, Vol. 1, pp. 99-133
3. b) Uemura, A., ibid., 1991, Vol. 2, pp. 99-133.
4. c) Baldoli, C.; Del Buttero, P.,; Di Ciolo, M.; Maiorana, S.; Papagni, A.; Synlett. 1996, 258-260.
5. d) Kunding, E. P.; He Xu, L.; Romanens, P.; Bernardinelli, G. Synlett. 1996, 270-272.
6. 3. Solladiè-Cavallo, A.; Solladiè, G.; Tsamo, E. J. Org. Chem., 1979, 44, 4189-4191.
7. 4. Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Tetrahedron: Asymmetry 1992, 3, 1303-1316.
8. 5. a) Aubé, I.; Heppert, J.A.; Milligan, M. L.; Smith, M. J.; Zenk, P.; J. Org. Chem. 1993, 58, 6182-6189.
9. b) Kundng, E. P.; Ripa, A.; Liu, R.; Amurrio, D., Bernardinelli, G. Organometallics 1993, 12, 3724-3737.
10. c) Kondo, J.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6183-6189.
11. 6. Davies, S. G.; Bromley, A. L.; Goodfellow G. L.; Tetrahedron: Asymmetry 1991, 2, 139-156.
12. 7. Arnoldi, A.; Carughi, M.; Synthesis, 1988, 155-157.
13. -1) 1880, 1960.
14. 3, Z=2, 3114 independent reflections were measured. The structure was solved using direct methods with the Shelx86 program. The non-hydrogen atoms were included in geometric positions and given thermal parameters equivalent to 1.2 times those of the atom to which they were attached. The structure was then refined using Shelxl to R1 of 0.0525 and wR2 of 0.2071. Coordinates have been deposited at the Cambridge Crystallographic Data Centre.
15. 2, r.t., air, sunlight.
16. 11. Column Chiralcel OD (Daicel), hexane/iPrOH 90:10 (v/v), flow 1ml/min ; UV detector, λ 254 nm.
17. 3) δ 3.8 (1H, s, OMe); 5.1 (2H, s, CH2); 6.5 (1H, s, CH); 6.9-7.5 (8H, m, arom). MS (EI): m/z (%) 258 (8), 215 (5), 135 (15), 122 (100).
18. 1H-NMR and MS spectra identical to those of(+)-5.