Selenosulfonation of Conjugated Enynes and the Enyne Equivalent l,4-Dichloro-2-butyne. Preparation of Sulfonyl-Substituted Allenic Alcohols and Dienes Using [2,3] Sigmatropic Rearrangements and Organocuprate Additions

Journal of Organic Chemistry

Volumn 55, Issue 15, 1990, Pages 4595-4602

  Back, Thomas G ^a   Lai, Enoch K Y ^a   Muralidharan, K Raman ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751554220     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00302a024     Document Type: Article

References (63)

1. For reviews, see: (a) The Chemistry of Sulphones and Sulph-oxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: Chichester, 1988.
2. De Lucchi, O.; Pasquato, L. Tetrahedron, 1988, 44, 67–85.
3. Trost, B. M. Bull. Chem. Soc. Jpn. 1988, 61, 107.
4. Block, E.; Aslam, M. Tetrahedron 1988, 44, 281.
5. Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903.
6. Durst, T. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: New York, 1979; Vol. 3, Chapter 11.9.
7. Magnus, P. D. Tetrahedron 1977, 33, 20–29.
8. Back, T. G.; Collins, S. J. Org. Chem. 1981, 46, 32–49.
9. Gancarz, R. A.; Kice, J. L. J. Org. Chem. 1981,46,48–99.
10. Kang, Y.-H.; Kice, J. L. J. Org. Chem. 1984. 49. 15–107.
11. Back, T. G.; Collins, S.; Kerr, R. G. J. Org. Chem. 1983, 48, 30–77.
12. Back, T. G.; Collins, S.; Gokhale, U.; Law, K.-W. J. Org. Chem. 1983, 48, 47–76.
13. Miura, T.; Kobayashi, M. J. Chem. Soc., Chem, Commun. 1982. 438.
14. Back, T. G.; Krishna, M. V.; Muralidharan, K. R. J. Org. Chem. 1989, 54, 41–46.
15. Back, T. G.; Collins, S.; Law, K.-W. Can. J. Chem. 1985, 63, 23–33.
16. Kice, J. L.; Kang, Y.-H. Tetrahedron 1985, 41, 47–89.
17. Backvall, J.-E.; Najera, C.; Yus, M. Tetrahedron Lett. 1988, 29, 14–45.
18. Back, T. G.; Muralidharan, K. R. J. Org. Chem. 1989, 54, 121.
19. For the first preparation of these compounds, see: (a) Foss, O. J. Am. Chem. Soc. 1947, 69, 22–36.
20. For more convenient methods, see ref 2b and: (b) Back, T. G.; Collins, S.; Krishna, M. V. Can. J. Chem. 1987, 65, 38.
21. For a review of [2,3] sigmatropic rearrangements of selenium compounds, see: Reich, H. J. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley: New York, 1987; Chapter 8.
22. See inter alia: (a) Djahanbini, D.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 34–41.
23. Kim, S. J.; Cha, J. K. Tetrahedron Lett. 1988, 29, 56–113.
24. Crandall, J. K.; Batal, D. J. Tetrahedron Lett. 1988, 29, 47–91.
25. Nikam, S. S.; Chu, K.-H.; Wang, K. K. J. Org. Chem. 1986, 51, 745.
26. For other preparations of allenic alcohols, see: Hopf, H. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley: Chichester, 1980; Part 2, pp 811–814.
27. Preliminary communication: Back, T. G.; Lai, E. K. Y.; Muralidharan, K. R. Tetrahedron Lett. 1989, 30, 64–81.
28. Andell, o. S.; Backvall, J.-E. Tetrahedron Lett. 1985,26,45–55.
29. Cuvigny, T.; Herve du Penhoat, C.; Julia, M. Tetrahedron 1986, 42, 53–129.
30. Backvall, J.-E.; Juntunen, S. K. J. Am. Chem. Soc. 1987,109, 63–96.
31. Backvall, J.-E.; Plobeck, N. A.; Juntunen, S. K. Tetrahedron Lett. 1989,30, 25–89.
32. Backvall, J.-E.; Rise, F. Tetrahedron Lett. 1989, 30, 53–147. For other cycloaddition reactions of sulfonyl dienes, see ref 14b and:
33. Chou, T.; Hung, S.-C. J. Org. Chem. 1988,53, 30–120.
34. Padwa, A.; Harrison, B.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1989, 54, 42–132.
35. Padwa, A.; Harrison, B.; Norman, B. H. Tetrahedron Lett. 1989, 30,32–59.
36. Padwa, A.; Norman, B. H. Tetrahedron Lett. 1988,29, 24–117.
37. Backvall, J.-E.; Juntunen, S. K. J. Org. Chem. 1988,53, 23–98.
38. Hardinger, S. A.; Fuchs, P. L. J. Org. Chem. 1987, 52, 27–39.
39. Strictly speaking, the methyl substituent of enyne 8 is at the 2-position as the olefin is assigned the lower number when both the double and triple bonds occur at the termini of the chain; see ref 17b. However, for the sake of consistency in discussions of compounds 6–8, we will consider the acetylenic carbon atoms to have the numbers 1 and 2.
40. Pine, S. Organic Chemistry, 5th ed.; McGraw Hill: New York, 1987; pp 64–65.
41. The assignment of the E and Z configurations was confirmed by their 1H NMR a-sulfonyl olefinic hydrogen signals, which occur farther downfield in the Z isomers. This was also observed previously in the case of a selenosulfonate adduct where the Z isomer was obtained by the base-catalyzed isomerization of the original E isomer. See ref 4.
42. Nonhebel, D. C.; Walton, J. C. Free-radical Chemistry; Cambridge University Press: Cambridge, 1974; pp 90–92.
43. It is surprising that the selenosulfonation of phenylacetylene (see ref 3a), where similar conjugation might be expected to stabilize the radical intermediate, is highly stereospecific (>97%) in favor of the E adduct.
44. For the preparation of other allenic alcohols via [2,3] sigmatropic rearrangements of selenoxides, see: Lerouge, P.; Paulmier, C. Tetrahedron Lett. 1984, 25, 19–87.
45. For a review of the stereochemistry of [2,3] sigmatropic rearrangements, see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1979, 18, 563.
46. For a study of the kinetics and stereochemistry of the [2,3] sigmatropic rearrangements of selenoxides, see: (b) Reich, H. J.; Yelm, K. E.; Wollowitz, S. J. Am. Chem. Soc. 1983, 105, 25–103.
47. An added complexity stems from the creation of a chiral center at the selenium atom when the achiral selenide is oxidized to the corresponding selenoxide. Although the present oxidation step produces a racemic selenoxide, we have arbitrarily shown only one enantiomer in Scheme II for simplicity. An asymmetric oxidation, followed by chirality transfer during the rearrangement, should result in the enantioselective formation of the allenic products. This possibility is under further investigation. For related work on chirality transfer during the [2,3] sigmatropic rearrangement of an allylic selenoxide, see: Davis, F. A.; Stringer, O. D.; McCauley, J. P., Jr. Tetrahedron 1985, 41, 47–147.
48. The precise mechanism for the equilibration is not known, but we also observed that the isomerization of pure trans-18 was promoted by the presence of benzeneseleninic acid (PhSe02H) and diphenyl diselenide (PhSeSePh), which are known to produce benzeneselenenic acid (PhSeOH) by comproportionation (see ref 24a,b). The latter compound, or its anhydride (see ref 24c,d), could presumably regenerate the selenenic ester from the allenic alcohol. (a) Reich, H. J.; Wollowitz, S.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43,16–97.
49. Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43,16–89.
50. Reich, H. J.; Willis, W. W., Jr.; Wollowitz, S. Tetrahedron Lett. 1982, 23, 33–119
51. Kice, J. L.; McAfee, F.; Slebocka-Tilk, H, Tetrahedron Lett. 1982, 23, 33–123
52. The 1H NMR signals of the two isomers were not sufficiently resolved to permit integration. However, the presence of two isomers was again confirmed by 13C NMR spectroscopy.
53. For the preparation of some other sulfur- and selenium-containing dienes by electrophilic addition to 4, followed by elimination, see: Bridges, A. J.; Fischer, J. W. J. Org. Chem. 1984, 49, 29–54.
54. Block, E.; Aslam, M. J. Am. Chem. Soc. 1983, 105, 61–64.
55. For a review, see: Petrzilka, M.; Grayson, J, I. Synthesis 1981, 753.
56. Chou, S.-S. P.; Sun, D.-J. J. Chem. Soc., Chem. Commun. 1988, 11–76.
57. A similar addition was recently used in the synthesis of a steroid side chain: Back, T. G.; Brunner, K.; Krishna, M. V.; Lai, E. K. Y. Can. J. Chem. 1989, 67, 10–32.
58. Derome, A. E. In Modern NMR Techniques for Chemistry Re-search: Pergamon Press: Oxford, 1987; Chapter 5.
59. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 29–123.
60. Koshino, J.; Sugawara, T.; Suzuki, A. Synth. Commun. 1984,14, 245.
61. Casaderall, E.; Jallageas, J.-C.; Mior, L.; Mior, M.; Moreau, P. C. R. Acad. Sci., Ser. C 1967, 265, 839.
62. Padwa, A.; Wannamaker, M. W.; Dyszlewski, A. D. J. Org. Chem. 1987, 52, 47–60.
63. Additional 1H NMR signals at δ 5.25 (s), 4.98 (s), and 3.92 (s) suggest the presence of the following compound in the crude reaction mixture: