Planar chiral organosulfur cycles

Chemistry Letters

Volumn 38, Issue 11, 2009, Pages 1028-1029

  Uehara, Kazuhiro ^a,b   Tomooka, Katsuhiko ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70349647599     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.1028     Document Type: Article

References (28)

1. a) I. Shcherbakova, A. F. Pozharskii, in Comprehensive Organic Functional Group Transformations II, ed. by A. R. Katritzky, R. J. K. Taylor, Elsevier, Oxford, 2005, Vol.2, pp. 89-235.
2. b) The Synthesis of Sulphones, Sulphoxides, and Cyclic Sulphides, ed. by S. Patai, Z. Rappoport, Wiley, New York, 1994.
3. c) N. S. Simpkins, in Sulphones in Organic Synthesis, ed. by J. E. Baldwin, P. D. Magnus, Pergamon, Oxford, 1993, p. 5.
4. d) Z. Jin, P. C. Vandort, P. L. Fuchs, Phosphorus, Sulfur, Silicon Relat. Elem. 1994, 95, 1.
5. e) E. N. Prilezhaeva, Russ. Chem. Rev. 2000, 69, 367.
6. a) H. Pellissier, Tetrahedron 2006, 62, 5559.
7. b) I. Fernández, N. Khiar, Chem. Rev. 2003,103, 3651.
8. c) C. Carreno, Chem. Rev. 1995, 95, 1717.
9. a) K. Tomooka, N. Komine, D. Fujiki, T. Nakai, S. Yanagitsuru, J. Am. Chem. Soc. 2005, 127, 12182.
10. b) K. Tomooka, M. Suzuki, M. Shimada, S. Yanagitsuru, K. Uehara, Org. Lett. 2006, 8, 963.
11. c) K. Tomooka, M. Suzuki, K. Uehara, M. Shimada, T. Akiyama, Synlett 2008, 2518.
12. d) K. Tomooka, T. Akiyama, P. Man, M. Suzuki, Tetrahedron Lett. 2008, 49, 6327.
13. I. D. Jenkins, S. Thang, Aust. J. Chem. 1984, 37, 1925.
14. Only a negligible amount of dimerized product (<1%) was formed in this reaction.
15. 3 at ambient temperature shows two sets of nonequivalent a-5-allylic geminai protons (at C2 and C9) 6.
16. The use of 5 equivalents of mCPB A caused the epoxidation of (E)-alkene moiety.
17. CHIRALPAK AD-H, hexane, UV 220 nm, rt.
18. The absolute configurations of 1-3 were speculated on the basis of the similarity of the measured CD spectra and the calculated CD spectra; see the Supporting Information.
19. Crystallographic data reported in this paper have been deposited with Cambridge Crystallographic Data Centre as supplementary publication Nos. CCDC-719699 [(PR*,S*s)-2], CCDC-719700 (3), CCDC-719698 [(PR*.,R*)-9]. Copies of the data can be obtained free of charge via http://www.ccdc. cam .ac .uk/conts/retrie ving .html.
20. CHIRALPAK AS-H, hexane/EtOH = 1/1, UV 220 nm, rt 11.
21. Mightysil Si 60 (5μm), hexane/i-PrOH = 4/1, UV 220 nm, rt.
22. We are not successful yet in separating the major diastereomer 2 into its enantiomers at the moment.
23. The pioneering work on thia-[2,3]-Wittig rearrangement: V. Rautenstrauch, Helv. Chim. Acta 1971, 54, 739;
24. For a review on the thia-Wittig rearrangement, see: K. Tomooka, in The Chemistry of Organolithium Compounds, ed. by Z. Rappoport, I. Marek, John Wiley & Sons, Ltd., Chichester, 2004, Vol.2, pp. 749-828.
25. A similar stereoselective transannular rearrangement of heterocyclic system had been reported, see: J. A. Marshall, J. Lebreton, J. Org. Chem. 1988, 53, 4108, Refs. 3a-3c.
26. The relative stereochemistry of 9 was determined as pR*,R* configuration based on X-ray analysis.
27. A possible explanation for this result should be originating from the stabilizing effect of a-sulfonyl group on the carbanion.
28. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/ index.html.