Addition of bis-sulfinyl anions to ketones: Stereoselective synthesis of allylic alcohols through Evans-Mislow rearrangement based domino reactions

Synthesis

Volumn , Issue 15, 2007, Pages 2273-2278

  Brebion, Franck ^a   Nàjera, Francisco ^a   Delouvrié, Bénédicte ^a   Lacôte, Emmanuel ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Alkenation; Carbanion; Pericyclic reaction; Sulfoxide; Sulfur

Indexed keywords

ALLYLIC ALCOHOLS; BIS-SULFINYL ANIONS; SULFINYL GROUPS;

ALCOHOLS; KETONES; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

NEGATIVE IONS;

(2,4) 4 TERT BUTYL 2 {[4 TOLYSULFINYL]METHYLENE}CYCLOHEXANOL; 2 {[4 TOLYLSULFINYL]METHYLENE}CYCLOPENTANOL; 2 {[4 TOLYSULFINYL]METHYLENE}CYCLOHEXANOL; ALLYL COMPOUND; ALLYLIC ALCOHOL; ANION; BASE; CYCLOHEXANE; CYCLOHEXANOL DERIVATIVE; CYCLOPENTANONE DERIVATIVE; KETONE; LITHIUM; PENTANOL; PIPERIDINE; SULFOXIDE; THIOPHENOL; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHIRALITY; DEGRADATION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 34547821937     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-966070     Document Type: Article

References (26)

1. (a) Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4869.
2. (b) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147.
3. (c) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl 1979, 18, 563.
4. For rearrangements involving sulfoxides, see: (d) Braverman, S. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; John Wiley: London, 1988, 717 .
5. For [2,3] sigmatropic rearrangements, see: (e) Ritter, K. In Houben-Weyl, 4th ed., Vol. E 21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 4971.
6. (a) Tanikaga, R.; Nozaki, Y.; Tamura, T.; Kaji, A. Synthesis 1983, 134.
7. (b) Ono, T.; Tamaoka, T.; Yuasa, Y.; Matsuda, T.; Nokami, J.; Wakabayashi, S. J. Am. Chem. Soc. 1984, 106, 7890.
8. (c) Nokami, J.; Kataoka, K.; Shiraishi, K.; Osafune, M.; Hussain, I.; Sumida, S.-I. J. Org. Chem. 2001, 66, 1228.
9. (d) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 3189.
10. (a) Burgess, K.; Henderson, I. Tetrahedron Lett. 1989, 30, 3633.
11. For a different and more selective cascade, see: (b) Arce, E.; Carreño, M. C.; Cid, M. B.; Garcìa Ruano, J. L. J. Org. Chem. 1994, 59, 3421.
12. (c) Carreño, M. C.; Cid, M. B.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1996, 7, 2151.
13. Guerrero-de la Rosa, V.; Ordoñez, M.; Alcudia, F.; Liera, J. M. Tetrahedron Lett. 1995, 36, 4889.
14. (a) Delouvrié, B.; Nájera, F.; Fensterbank, L.; Malacria, M. J. Organomet. Chem. 2002, 643-644, 130.
15. (b) Brebion, F.; Vitale, M.; Fensterbank, L.; Malacria, M. Tetrahedron: Asymmetry 2003, 14, 2889.
16. (c) Brebion, F.; Delouvrié, B.; Nájera, F.; Fensterbank, L.; Malacria, M.; Vaissermann, J. Angew. Chem. Int. Ed. 2003, 42, 5342.
17. (d) Brebion, F.; Goddard, J.-P.; Fensterbank, L.; Malacria, M. Synthesis 2005, 2449.
18. (e) Brebion, F.; Goddard, J.-P.; Gomez, C.; Fensterbank, L.; Malacria, M. Synlett 2006, 713.
19. Additions of the anion derived from Aggarwal's cyclic bissulfoxide to not to sterically demanding ketones led to the corresponding bis-sulfinyl alcohols, without further reaction: Aggarwal, V. K.; Franklin, R.; Maddock, J.; Evans, G. R.; Thomas, A.; Mahon, M. F.; Molloy, K. C.; Rice, M. J. J. Org. Chem. 1995, 60, 2174.
20. Sugimura, T.; Iguchi, H.; Tsuchida, R.; Tai, A.; Nishiyama, N.; Hakushi, T. Tetrahedron: Asymmetry 1998, 9, 1007.
21. The properties of alkene carbenium ions and carbanions: Richey, H. G. J. In The Chemistry of Alkenes, Vol. 2; Zabicky, J., Ed.; John Wiley: London, 1970, 39.
22. (a) Annunziata, R.; Cinquini, M.; Cozzi, F.; Farina, S.; Montanari, V. Tetrahedron 1987, 43, 1013.
23. (b) Koprowski, M.; Krawczyk, E.; Skowroñska, A.; McPartlin, M.; Choi, N.; Radojevic, S. Tetrahedron 2001, 57, 1105.
24. (c) Zohar, E.; Stanger, A.; Marek, I. Synlett 2005, 2239.
25. Hoffmann, R. W.; Goldmann, S.; Gerlach, R.; Maak, N. Chem. Ber. 1980, 113, 845.
26. Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599.