Phosphazene base P2-Et mediated isomerization of vinyl sulfones to allyl sulfones

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5247-5248

  Jin, Zhendong ^a   Kim, Seong Heon ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598011     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01110-0     Document Type: Article

References (9)

1. 1 Syntheses via vinyl sulfones 64.
2. 2 (a) Mine, J., Skoglund, M. J. J. Org. Chem. 1982, 47, 4766;
3. (b) Mine, J.; Linden, S.-M., Wang, A., Thiagarajan, V. J. Org. Chem. 1980, 45, 2821.
4. 3 (a) Schwesinger, R., Schlemper, H. Angew. Chem. 1987, 99, 1212;
5. (b) Schwesinger, R. Chimia. 1985, 39, 269;
6. (c) Pietzonka, T., Seebach, D. Chem. Ber. 1991, 124, 1837;
7. (d) Schwesinger, R., Willaredt, J., Schlemper, H., Keller, M., Schmitt, D., Fritz H. Chem. Ber. 1994, 127, 2435 and references cited therein. (figure presented)
8. 4 The only product isolated from the reaction of 4 with catalytic amount of KO-t-Bu was compound 18. This is consistent with our observation that 5 membered-ring vinyl sulfones are good Michael acceptors. The major product isolated from the reaction of 10 with a catalytic amount of was compound 19. For additional examples of this reaction, see Jin, Z., Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 3022; and Kim, S. H., Jin, Z. Fuchs, P. L. Tetrahedron Lett. 1995, 36, 4537.
9. 4 The only product isolated from the reaction of 4 with catalytic amount of KO-t-Bu was compound 18. This is consistent with our observation that 5 membered-ring vinyl sulfones are good Michael acceptors. The major product isolated from the reaction of 10 with a catalytic amount of was compound 19. For additional examples of this reaction, see Jin, Z., Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 3022; and Kim, S. H., Jin, Z. Fuchs, P. L. Tetrahedron Lett. 1995, 36, 4537.