Straightforward synthesis of strained α,β-epoxysulfones via epoxidation of vinylsulfones using N-methylmorpholine N-oxide as epoxidizing reagent

Synlett

Volumn , Issue 12, 2007, Pages 1948-1950

  Rincón, Rocío ^a   Aljarilla, Ana ^a   Criado, María ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

, epoxysulfone; Epoxidation; N methylmorpholine N oxide; Vinylsulfone

Indexed keywords

4 METHYLMORPHOLINE N OXIDE; ALPHA,BETA EPOXYSULFONE DERIVATIVE; MORPHOLINE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYLSULFONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; EPOXIDATION; STEREOCHEMISTRY;

EID: 34547632935     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984496     Document Type: Article

References (32)

1. (a) Review: Arjona, O.; Plumet, J. Curr. Org. Chem. 2002, 6, 571.
2. For other comprehensive reviews on the synthetic applications of oxa- and azanorbornene derivatives, see: (b) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521.
3. (c) Vogel, P. Curr. Org. Chem. 2000, 65, 455.
4. (d) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2002, 611.
5. (e) Medel, R.; Plumet, J. In Targets in Heterocyclic Systems, Vol. 8; Attanasi, O. A.; Spinelli, D., Eds.; Società Chimica Italiana, 2004, 162-186.
6. (f) Ishikura, M.; Katagiri, N. Recent Res. Dev. Org. Chem. 2004, 8, 197.
7. (g) Robina, I.; Vogel, P. Synthesis 2005, 675.
8. (h) Vogel, P. In The Organic Chemistry of Sugars; Levy, D. E.; Fugedi, P., Eds.; Taylor and Francis Group/CRC Press: Boca Ratón, 2006, Chap. 13, 629-725.
9. Arjona, O.; de Dios, A.; de la Pradilla, R. F.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906.
10. Arjona, O.; León, M. L.; Plumet, J. Org. Lett. 2000, 2, 3683.
11. (a) Arjona, O.; Borrallo, C.; Iradier, F.; Medel, R. Tetrahedron Lett. 1998, 39, 1977.
12. (b) Arjona, O.; Iradier, F.; Medel, R.; Plumet, J. Tetrahedron: Asymmetry 1999, 10, 3431.
13. (c) Arjona, O.; Lorenzo, G.; Medel, R.; Plumet, J. Tetrahedron Lett. 2001, 42, 7041.
14. Arjona, O.; Iradier, F.; Plumet, J.; Martínez-Alcázar, M. P.; Hernández-Cano, F.; Fonseca, I. Tetrahedron Lett. 1998, 39, 8335.
15. Arjona, O.; Menchaca, R.; Plumet, J. J. Org. Chem. 2001, 66, 2400.
16. Leung-Toung, R.; Liu, Y.; Muchowski, J. M.; Wu, Y. L. J. Org. Chem. 1998, 63, 3235.
17. (a) Simpkins, N. L. In Sulfones in Organic Synthesis, Tetrahedron Organic Chemistry Series; Pergamon Press: Oxford, 1993.
18. For some more recent references, see: (b) Diez, D.; Beneitez, M. T.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Sanz, F.; Broughton, H. B.; Urones, J. G. Org. Lett. 2003, 5, 4361.
19. (c) Diez, D.; Beneitez, M. T.; Gil, M. J.; Moro, R. F.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Urones, J. G. Synthesis 2005, 565.
20. For some synthetically useful transformations of this kind of compound, see: (a) Arjona, O.; Menchaca, R.; Plumet, J. Tetrahedron 2000, 56, 3901.
21. (b) Hodgson, D. M.; Maxwell, C. R.; Wisedate, R.; Matthews, I. R.; Carpenter, K. J.; Dickenson, A. H.; Wonnacott, S. J. Chem. Soc., Perkin Trans. 1 2001, 3150.
22. (a) Simpkins, N. L. In Sulfones in Organic Synthesis, Tetrahedron Organic Chemistry Series; Pergamon Press: Oxford, 1993, 55-58.
23. 2, 20°C, 4 h) provides the exo-epoxide 15 without the formation of Baeyer-Villiger oxidation product (Scheme 3). See: Prakash Rao, H. S.; Murali, R.; Taticchi, A.; Scheeren, H. W. Eur. J. Org. Chem. 2001, 2869. (Chemical Equation Presented)
24. The exo selectivity in the nucleophilic additions and cycloadditions of the bicyclo[2.21]heptene double bond is a characteristic behavior of these compounds. For a comprehensive discussion, see: Huisgen, R. Pure Appl. Chem. 1981, 53, 171; see in particular p. 181 and following.
25. Four isolated cases regarding the epoxidation reaction of α,β-unsaturated esters 16 with an amine oxide (NMO) to give endo-epoxides 17 (Scheme 4) have been previously described. See: Andres, C. J.; Spetseris, N.; Norton, J. R.; Meyers, A. J. Tetrahedron Lett. 1995, 36, 1613. (Chemical Equation Presented)
26. Compounds 4 and 5 were synthesized by cycloaddition reaction of p-toluenesulfonylacetylene with furan and N-BOC pyrrole, respectively: (a) Compound 4: Arjona, O.; Iradier, F.; Medel, R.; Plumet, J. Heterocycles 1999, 50, 653.
27. (b) Compound 5: Altenbach, H. J.; Blech, B.; Marco, J. A.; Vogel, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 778.
28. (c) See also: Chen, Z.; Trudell, M. L. Tetrahedron Lett. 1994, 35, 9649.
29. (d) In the same fashion, cycloaddition of cyclopentadiene and p-toluenesulfonylacetylene gave 6 in 99% isolated yield. Compound 7 (30% isolated yield) was prepared by trapping of isobenzofuran 22 [generated by reaction of 3,6-di(2′-pyridyl)-5- tetrazine(19) with 1,4-dihydro-1,4-endoxynaphthalene (20)] with p-toluenesulfonylacetylene (Scheme 5). Analogous generation and trapping of N-Boc isoindole 23 gave compound 8 (62%). To the best of over knowledge these are the first cases concerning the application of the 'tetrazine method' to the synthesis of bicyclic α,β-unsaturated sulfones. Full details of the procedure will be reported in due course or upon request.
30. (e) For the generation of isobenzofuran, see: Warrener, R. N. J. Am. Chem. Soc. 1971, 93, 2346.
31. (f) For the generation of N-Boc isoindole, see: Priestly, G. M.; Warrener, R. N. Tetrahedron Lett. 1972, 4295. (Chemical Equation Presented)
32. 2 (6 mL), NMO (0.86 mmol) was added in one portion under argon at 0°C. The mixture was allowed to react at r.t. during 24 h. After this time the solvent was removed under reduced pressure and the residual material was purified by column chromatography (hexane-EtOAc, 4:1).