Use of phosphazene base and phase-transfer conditions for regiospecific alkylative isomerization of vinyl sulfones capable of undergoing β-elimination reactions

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5249-5252

  Jin, Zhendong ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598061     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01111-2     Document Type: Article

References (13)

1. 1 Synthesis via vinyl sulfones 65.
2. 2 (a) Burkholder, T. P.; Fuchs, P. L. J. Am. Chem. Soc. 1988, 110, 2341;
3. (b) Burkholder, T. P.; Fuchs, P. L. J. Am. Chem. Soc. 1990, 112, 9601.
4. 3 Jin, Z.; Fuchs, P. L., Tetrahedron Lett. 1993, 34, 5205.
5. 4 (a) Schwesinger, R.; Schlemper, H. Angew. Chem. Int. Ed. Engl. 1987, 26, 1167;
6. (b) Schwesinger, R. Chimia 1985, 39, 269;
7. (c) Pietzonka, T.; Seebach, D. Chem. Ber. 1991, 124, 1837;
8. (d) Schwesinger, Willaredt, J., R.; Schlemper, H., Keller, M., Schmitt, D., Fritz H. Chem. Ber. 1994, 127, 2435; and references cited therein.
9. 5 Jin, Z. Kim, S. H., Fuchs Tetrahedron Lett. 1996, 37, 0000. Preceding paper.
10. 6 Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208.
11. 7 (a) Golinski, J.; Jonczyk, A.; Makosza, M. Synthesis 1979, 461;
12. (b) Jonczyk, A.; Radwan-Pytlewski, T. J. Org. Chem. 1983, 48, 910.
13. 2 (large excess) and some minor side products. This mixture was further purified via Kugelrohr distillation (0.02 mm Hg at 130°C) to afford a mixture of the desired product and small amounts of the side products which can be further purified by flash column chromatography on silica gel to give 180 mg of pure adduct 15 (81%).