Stereodivergent C-C bond formation on arene-chromium template: Endo-selective allylation by Hosomi-Sakurai reaction

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8362-8363

  Sur, Surojit ^a   Ganesh, Sambasivam ^a,b   Pal, Debnath ^a   Puranik, Vedavati G ^a   Chakrabarti, Pinak ^a   Sarkar, Amitabha ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b SYNGENE INTERNATIONAL LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001321656     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961353c     Document Type: Article

References (24)

1. Reviews on arene tricarbonylchromium complexes: (a) Semmelhack, M. F. Transition Metal Arene Complexes: Nucleophilic Additions. In Comp. Organomet. Chem. II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 979. (b) Davies, S. G.; McCarthy, T. D. Transition Metal Arene Complexes: Side Chain Activation and Control of Stereochemistry. Ibid. p 1039.
2. Reviews on arene tricarbonylchromium complexes: (a) Semmelhack, M. F. Transition Metal Arene Complexes: Nucleophilic Additions. In Comp. Organomet. Chem. II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 979. (b) Davies, S. G.; McCarthy, T. D. Transition Metal Arene Complexes: Side Chain Activation and Control of Stereochemistry. Ibid. p 1039.
3. 6 arene) chromium Complexes in Organic Synthesis. In Advances In Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 231-240 and refs 84-110 cited therein.
4. (a) Ganesh, S.; Sarkar, A. Tetrahedron Lett. 1991, 32, 1085.
5. (b) Uemura, M.; Oda, H.; Minami, T.; Hayashi, Y. Tetrahedron Lett. 1991, 32, 4565.
6. (c) Uemura, M.; Oda, H.; Minami, T.; Shiroo, M.; Hayashi, Y. Organometallics 1992, 11, 3705.
7. Ganesh, S.; Sathe, K. M.; Nandi, M.; Chakrabarti, P.; Sarkar, A. J. Chem. Soc., Chem. Commun. 1993, 224.
8. For reviews on the Hosomi-Sakurai reaction: (a) Hosomi, A. Acc. Chem. Res. 1988, 21, 200. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.: Pergamon: Oxford, 1991; Vol. 1, p 579. (c) Yamamoto, Y.; Sasaki, N. In Stereochemistry of Organometallic and Inorganic Compounds; Berna, I., Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 363.
9. For reviews on the Hosomi-Sakurai reaction: (a) Hosomi, A. Acc. Chem. Res. 1988, 21, 200. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.: Pergamon: Oxford, 1991; Vol. 1, p 579. (c) Yamamoto, Y.; Sasaki, N. In Stereochemistry of Organometallic and Inorganic Compounds; Berna, I., Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 363.
10. For reviews on the Hosomi-Sakurai reaction: (a) Hosomi, A. Acc. Chem. Res. 1988, 21, 200. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.: Pergamon: Oxford, 1991; Vol. 1, p 579. (c) Yamamoto, Y.; Sasaki, N. In Stereochemistry of Organometallic and Inorganic Compounds; Berna, I., Ed.; Elsevier: Amsterdam, 1989; Vol. 3, p 363.
11. On photolysis at 350 nm for 5 h in chloroform-d, 2-(p-tolylidene)-1-tetralone afforded a mixture of stereoisomers. The olefinic proton in each appears at 6.8 and 7.85 ppm, confirming the assignment of olefin geometry in complexes 1a and 1b. In rigid and stereochemically defined structures such as isomeric α-benzylidenecamphors, the chemical shift of the syn (with respect to the carbonyl group) olefinic proton is 7.4 ppm while that of the anti olefinic proton is 6.45 ppm: Kossanyi, J.; Furth, B.; Morizur, J. P. Tetrahedron 1970, 26, 395. The deshielding of the syn olefinic proton is ascribed to the deshielding effect of the carbonyl group anisotropy.
12. See ref 1b for refs 13-22 and 32-33 cited therein.
13. Reviews on oxy-anionic Cope rearrangement: (a) Wilson, S. R. Anion Assisted Sigmatropic Rearrangements. In Org. React. 1993, 43, 93. (b) Hill, R. K. Cope, oxy-Cope and Anionic oxy-Cope Rearrangements. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 785.
14. Reviews on oxy-anionic Cope rearrangement: (a) Wilson, S. R. Anion Assisted Sigmatropic Rearrangements. In Org. React. 1993, 43, 93. (b) Hill, R. K. Cope, oxy-Cope and Anionic oxy-Cope Rearrangements. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 785.
15. For a discussion of Lewis acid complexation directing stereochemical outcome in arene-chromium complexes, see ref 3b,c.
16. Crystal structures reveal planar coordination of Lewis acids to the carbonyl group: (a) Brun, L. Acta Crystallogr. 1966, 26739. (b) Bullock, R. M.; Rappoli, B. J.; Samsel, E. G.; Rheingold, A. L. J. Chem. Soc., Chem. Commun. 1989, 261. (c) Bochmann, M.; Webb, K. J.; Hursthouse, M. B.; Mazid, M. J. Chem. Soc., Chem. Commun. 1991, 1735.
17. Crystal structures reveal planar coordination of Lewis acids to the carbonyl group: (a) Brun, L. Acta Crystallogr. 1966, 26739. (b) Bullock, R. M.; Rappoli, B. J.; Samsel, E. G.; Rheingold, A. L. J. Chem. Soc., Chem. Commun. 1989, 261. (c) Bochmann, M.; Webb, K. J.; Hursthouse, M. B.; Mazid, M. J. Chem. Soc., Chem. Commun. 1991, 1735.
18. Crystal structures reveal planar coordination of Lewis acids to the carbonyl group: (a) Brun, L. Acta Crystallogr. 1966, 26739. (b) Bullock, R. M.; Rappoli, B. J.; Samsel, E. G.; Rheingold, A. L. J. Chem. Soc., Chem. Commun. 1989, 261. (c) Bochmann, M.; Webb, K. J.; Hursthouse, M. B.; Mazid, M. J. Chem. Soc., Chem. Commun. 1991, 1735.
19. (a) For a review on Lewis acid-carbonyl complexation, see: Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, p 283.
20. (b) Detailed spectroscopic studies on Lewis acid-carbonyl complexes have been carried out by Denmark in order to probe stereoselectivity in Lewis acid-promoted reactions. See: Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133. Also see: Denmark, S. E.; Almstead, N. G. Tetrahedron 1992, 48, 5565 and refs 12 and 13 cited therein.
21. (b) Detailed spectroscopic studies on Lewis acid-carbonyl complexes have been carried out by Denmark in order to probe stereoselectivity in Lewis acid-promoted reactions. See: Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133. Also see: Denmark, S. E.; Almstead, N. G. Tetrahedron 1992, 48, 5565 and refs 12 and 13 cited therein.
22. A study, with extensive references, on the importance of out-of-plane complexation of titanium in promoting organic reactions recently appeared: Singh, D. K.; Springer, J. B.; Goodson, P. A.; Corcoran, R. C. J. Org. Chem. 1996, 61, 1436. Reference 21a-i in this paper provides a collection of relevant dihedral angle data from CSD.
23. 4, no reaction took place between allyltrimethylsilane and the substrate, and the starting material was quantitatively recovered. Thus, the dependence of selectivity on Lewis acid could not be addressed.
24. This possibility has been suggested in the context of Lewis acid carbonyl complexation: ref 13a, p 283.