(Alkoxyallyl)sulfones as enal and enone β-anion equivalents. Synthesis of mono-, di- and trisubstituted furans

Tetrahedron

Volumn 52, Issue 48, 1996, Pages 15289-15310

  Craig, Donald ^a   Etheridge, Christopher J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030602246     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00932-5     Document Type: Article

References (14)

1. 1. Craig, D.; Etheridge, C. J.; Smith, A. M., preceding paper.
2. 2. Inomata and co-workers have reported a related strategy by which 3-monosubstituted furans are constructed from a 2-[(4-tolylsulfonyl)ethyl]-1,3-dioxolane, haloalkanes and paraformaldehyde: Inomata, K.; Aoyama, S.-I.; Kotake, H. Bull. Chem. Soc. Jpn. 1978, 51, 930. For a method for the synthesis of 3-acylfurans using related sulfide-containing reagents, see: Inomata, K.; Sumita, M.; Kotake, H. Chem. Lett. 1979, 709.
3. 2. Inomata and co-workers have reported a related strategy by which 3-monosubstituted furans are constructed from a 2-[(4-tolylsulfonyl)ethyl]-1,3-dioxolane, haloalkanes and paraformaldehyde: Inomata, K.; Aoyama, S.-I.; Kotake, H. Bull. Chem. Soc. Jpn. 1978, 51, 930. For a method for the synthesis of 3-acylfurans using related sulfide-containing reagents, see: Inomata, K.; Sumita, M.; Kotake, H. Chem. Lett. 1979, 709.
4. 3. Preliminary communication: Craig, D.; Etheridge, C. J. Tetrahedron Lett. 1993, 34, 7487.
5. 4. For an analogous one-pot method for the preparation of vinylic sulfones, see: Lee, J. W.; Oh, D. Y. Synth. Commun. 1989, 19, 2209; we thank a referee for bringing this work to our attention. For related methodology applied to the synthesis of vinylic sulfoxides and sulfoximines, see respectively: Craig, D.; Daniels, K.; Marsh, A.; Rainford, D.; Smith, A. M. Synlett 1990, 531, and Craig, D.; Geach, N. J. Synlett 1992, 299.
6. 4. For an analogous one-pot method for the preparation of vinylic sulfones, see: Lee, J. W.; Oh, D. Y. Synth. Commun. 1989, 19, 2209; we thank a referee for bringing this work to our attention. For related methodology applied to the synthesis of vinylic sulfoxides and sulfoximines, see respectively: Craig, D.; Daniels, K.; Marsh, A.; Rainford, D.; Smith, A. M. Synlett 1990, 531, and Craig, D.; Geach, N. J. Synlett 1992, 299.
7. 4. For an analogous one-pot method for the preparation of vinylic sulfones, see: Lee, J. W.; Oh, D. Y. Synth. Commun. 1989, 19, 2209; we thank a referee for bringing this work to our attention. For related methodology applied to the synthesis of vinylic sulfoxides and sulfoximines, see respectively: Craig, D.; Daniels, K.; Marsh, A.; Rainford, D.; Smith, A. M. Synlett 1990, 531, and Craig, D.; Geach, N. J. Synlett 1992, 299.
8. 5. Unstable product. Yields cited are for crude materials.
9. 6. No TMEDA was used in the formation of 7g.
10. 7. Buchta, E.; Huhn, C. Liebigs Ann. Chem. 1965, 687, 161.
11. 8. Srikrishna, A.; Sunderbabu, G. Chem. Lett. 1988, 371.
12. 9. Srikrishna, A.; Sunderbabu, G. Tetrahedron Lett. 1987, 28, 6393.
13. 10. Batt, D. G.; Jones, D. G.; La Greca, S. J. Org. Chem. 1991, 56, 6704.
14. 11. Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655.