Asymmetric Heck reaction of (R) 1-tert-butylsulfinylcyclopentene with arenediazonium salts

Synlett

Volumn , Issue 10, 1999, Pages 1603-1605

  Priego, Julián ^a   Carretero, Juan Carlos ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Asymmetric synthesis; Chiral cyclopentenes; Diazoniums salts; Heck reaction; Sulfoxides

Indexed keywords

CYCLOPENTENE DERIVATIVE; DIAZONIUM COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFOXIDE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; STEREOCHEMISTRY;

EID: 0032822797     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2890     Document Type: Article

References (35)

1. Recent reviews on the Heck reaction: a) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth., 1996, 3, 447.
2. b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
3. c) de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 36, 2379.
4. d) Bräse, S.; de Meijere, A. In Metal-catalyzed Crosscoupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
5. For a review on the asymmetric Heck reaction, see: Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. For some recent references, see: a) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
6. For a review on the asymmetric Heck reaction, see: Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371. For some recent references, see: a) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
7. b) Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. Synthesis 1998, 581.
8. c) Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 1338.
9. c) Cheng, C.-Y.; Liou, J.-P.; Lee, M.-J. Tetrahedron Lett. 1997, 38, 4571.
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12. For some recent results on the use of the tert-butylsulfinyl group as a chiral auxiliary in other reactions, see: a) Cogan D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268.
13. b) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
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16. 3 (2 equiv)] in acetonitrile at 60°C for 72h. Furthermore, the stereoselectivity was significantly lower than from p-methoxybenzenediazonium tetrafluoroborate (2A:2B = 17:83 instead of 9:91).
17. For recent references on aryldiazonium salts in Heck reactions, see: a) Oliveira, D. F.; Severino, E. A.; Correia, C. R. D. Tetrahedron Lett. 1999, 40, 2083.
18. b) Sengupta, S.; Sadhukhan, S. K. Tetrahedron Lett. 1998, 39, 715.
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20. d) Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S. Tetrahedron 1997, 53, 2213.
21. 3 as additive in the Heck reaction of arenediazonium salts had not been described previously.
22. 6), significant signals: δ = 6.09 (br s, 1H), 4.11 (br s, 1H), 1.08 (s, 9H).
23. 2 for the case of the diazonium salts of entries 3 and 4 of Table 2.
24. For examples of Heck reactions of cyclopentene, see: a) Larock, R. C.; Baker, B. E. Tetrahedron Lett. 1988, 29, 905.
25. b) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603.
26. c) Prashad, M.; Tomesch, J. C.; Wareing, J. R.; Smith, H. C.; Cheon, S. H. Tetrahedron Lett. 1989, 30, 2877.
27. d) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31
28. We confirmed that, as expected, substrate 1 (ee = 96%, HPLC, chiralpak AS) did not suffer racemization at sulfur under these experimental Heck reactions, as it was proved by the preservation of the same high optical purity in the adduct 3B (ee = 96% by HPLC, Chiralccl OD).
29. 3)
30. Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 1338.
31. 2/NaH/t-AmOH].
32. Fabre, J. L.; Julia, M. Tetrahedron Lett. 1983, 4311.
33. This moderate yield was mainly due to the high volatility of cyclopentene 11.
34. Recent ab initio calculations performed on different substituted α,β-unsaturated sulfoxides indicate that the s-cis conformation is significantly more stable than any other (Tietze, L. F.; Schuffenhauer, A.; Schreiner, P. R. J. Am. Chem. Soc. 1998, 120, 7952).
35. For a similar result in the Heck reactions of nitro-substituted diazonium compounds, see: Sengupta, S.; Bhattacharya, S. J. Chem. Soc. Perkin Trans. 1 1993, 1943.