Synthesis of bis(enolnonaflates) and their 4-exo-trig-cyclizations by intramolecular Heck reactions

Synlett

Volumn , Issue 10, 1999, Pages 1654-1656

  Bräse, Stefan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric Heck reaction; Cascade reaction; Cyclobutanes; Desymmetrization

Indexed keywords

BUTANE; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344132082     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2892     Document Type: Article

References (33)

1. Bräse S; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions. Diederich, F; Stang, P. J., Ed; Wiley-VCH: Weinheim; 1998, p. 99-166.
2. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
3. Heck, R. F.; Nolley, J. P. Jr. J. Org. Chem. 1972, 37, 2320-2322.
4. Heck, R. F. Acc. Chem. Res. 1979, 12, 146-151.
5. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
6. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
7. Ang, K. H.; Bräse, S; Steinig, A. G.; Meyer, F. E.; Llebaria, A.; Voigt, K.; de Meijere, A. Tetrahedron 1996, 52, 11503-11528.
8. Grigg, R.; Stevenson, P.; Worakun, R. Tetrahedron 1988, 44, 2033-2048.
9. Mahajan, J. R. J. Chem. Soc. Perkin Trans. I 1978, 1434-1437.
10. Hirsch, E.; Hünig, S; Reißig, H. U. Chem. Ber. 1982, 115, 3687-3696.
11. Webel, M.; Reißig, H. U. Synlett 1997, 1141-1142.
12. Bräse, S.; de Meijere, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 2545-2545.
13. Ritter, K. Synthesis 1993, 735-762.
14. The synthesis of 1,2-bisenol(triflates) have been reported previously: Voigt, K. Diplomarbeit Universität Göttingen Germany 1992.
15. Kirwan, J. N.; Roberts, B. P. J. Chem. Soc. Perkin Trans 2 1989, 539-550.
16. Gleiter, R.; Doerner, T.; Irngartinger, H. Liebigs Ann. 1996, 381-392.
17. Curran, D. P. Angew. Chem. Int. Ed. 1998, 110, 1174-1196.
18. 28: C. 91.08; H. 8.92; found C 90.89, H 8.65.
19. Macor, J. E.; Ogilvie, R. J.; Wythes, M. J. Tetrahedron Lett. 1996, 37, 4289-4292.
20. For examples which include unsuccessful cyclization attempts: Narula, C. K.; Mak, K. T.; Heck, R. F. J. Org. Chem. 1983, 48, 2792-2796.
21. Grigg, R.; Sridharan, V.; Sukirthalingam, S. Tetrahedron Lett. 1991, 32, 3855-3858.
22. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846-5848
23. Overman, L. E.; Renaldo, A. F. J. Am. Chem. Soc. 1990, 112, 3945-3949.
24. Gajewski, J. J.; Benner, C. W.; Stahly, B. N.; Hall, R. F.; Sato, R. I. Tetrahedron 1982, 38, 853-862.
25. The dihedral angle of the diene moiety was determined to be 34.9° by AMI or 41. 9° by MINDO/3 calculations, respectively.
26. This ester is superior over the methyl or ethyl analogue in Heck coupling reactions because of the higher boiling point.
27. For intermolecular examples: Kamikawa, T.; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 3161 -3164. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
28. For intermolecular examples: Kamikawa, T.; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 3161 -3164. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
29. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419.
30. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. For a review see: Shibasaki, M.; Boden, C. D. J; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
31. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. For a review see: Shibasaki, M.; Boden, C. D. J; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
32. The enantiomeric excesses were determined by stationary chiral HPLC ([(S,S)-WHELK-O], cyclohexane/iso-propanol 99:1; 254 nm).
33. The following chiral ligands have been used for the synthesis of 5 so far: BINAP (27% ee, 57% yield), DIOP (18% ee, 42% yield), PHANEPHOS (37% ee, 23% yield), i-propyloxazoline (see ref 1: ligand developed by Helmchen et al., Pfaltz et al. and Williams et al.) (52% ee, 25% yield).