Stereochemistry of the formation of endocyclic sulfoximides from o-carboxyphenyl sulfoxides

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 361-364

  Allenmark, Stig ^a   Claeson, Sofia ^a   Löwendahi, Christina ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZISOTHIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030040171     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00006-7     Document Type: Article

References (18)

1. (a) Stoss, P.; Satzinger, G. Angew. Chem. 1971, 83, 83. See also:
2. (b) Kennewell, P.D.; Taylor, J.B. Chem. Soc. Rev. 1975, 4, 189.
3. (c) Kennewell, P.D.; Taylor, J.B. Chem. Soc. Rev. 1980, 9, 477.
4. Johnson, C.R.; Janiga, E.R. J. Am. Chem. Soc. 1973, 95, 7692.
5. Johnson, C.R.; Kirchhoff, R.A.; Corkins, H.G. J. Org. Chem. 1974, 39, 2458.
6. Allenmark, S.; Andersson C.; Widell, P. Chirality 1995, 7, 541.
7. MSH was prepared via acid hydrolysis of ethyl O-(mesitylenesulfonyl)acetohydroxamate (see: (a) Tamura, Y.; Minamikawa, J.; Sumoto, K. Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239.
8. (b) Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1) using the modified method described by Johnson (see ref. 3).
9. MSH (160 mg) was dissolved in 5 ml of 1,2-dichloroethane, the solution was dried with magnesium sulfate and then filtered. The filtrate was placed in a water-bath at 55°C and a solution of (-)-(S)-1 (142 mg, 0.5 mmol) in 3 ml of 1,2-dichloroethane was then added dropwise under stirring. After the addition heating (to 60°C) was continued for 3 h. After cooling the reaction mixture was poured into 25 ml of 1 M sodium carbonate solution and shaken. The lower organic phase was washed with water, dried (MgSO4), filtered and the solvent evaporated, which yielded a crystalline product (81 mg, 57%) identified as (+)-2 in 94.3% stereochemical yield (89% e.e.).
10. An HPLC system incorporating an analytical (4.6 mm ID × 150 mm) column packed with a chiral sorbent based on crosslinked BSA (see: Allenmark, S.; Andersson, S. Chromatographia 1991, 31, 429) was used. The mobile phase consisted of 16 mM phosphate buffer (pH 8.0) containing 12% (v/v) acetonitrile as retention modifier at a flow rate of 1.2 ml/min. UV-detection at 230 nm was used throughout. Peak areas were determined by a Millipore/Waters mod. 740 integrator interfaced with the detector.
11. (a) Allenmark, S.; Hagberg, C.-E. Acta Chem. Scand. 1970, 24, 2225.
12. (b) Allenmark, S. Int. J. Sulfur Chem. 1973, 8, 127.
13. (c) Bohman, O.; Allenmark, S. Tetrahedron Lett. 1973, 405.
14. (d) Bohman, O.; Allenmark, S. Chem. Scr. 1973, 4, 202.
15. (a) Wilen, S.H. Tables of Resolving Agents and Optical Resolutions, University of Notre Dame Press, Notre Dame/London 1972.
16. (b) Newman, P. Optical Resolution Procedures for Chemical Compounds, vol. 4, Optical Resolution Information Center, Manhattan College, Riverdale, New York 1993.
17. Allenmark, S., Andersson, S., Möller, P., Sanchez, D. Chirality 1995, 7, 248.
18. Resolution of (±)-1 was was achieved by a single load of 0.98 g racemate on a 50 mm i.d. × 250 mm axially compressed Prochrom column containing a chiral sorbent made from crosslinked N,N'-diallyl L-tartardiamide (DATD) bis-(3,5-dimethylbenzoate) immobilized to 10 μm 150 Å Kromasil and elution with hexane/THF (80/20 v/v) containing 0.05% TFA. This gave 0.35g of (+)-(R)-1 in 99.8% e.e. and 0.38 g of (-)-(S)-1 in 97.1% e.e.