Synthesis of chiral organotin reagents: Diels–Alder reactions of methyl 3-(triphenylstannyl)acrylate: synthesis of diphenyl(3-substituted bicyclo[2.2.1]heptan-2-yl)tin hydrides

Abstract

Cyclopentadiene undergoes Diels–Alder reactions with methyl (E )- and (Z )-3-(triphenylstannyl)acrylates 5 and 6 to give the endo-cycloadduct 9, and a mixture of the exo- and endo-isomers 10 and 11, respectively. The endo-product 9 is reduced to the alcohol 12 which is protected as its methyl ether 13. Attempts to remove one of the phenyl substituents from the tin using iodine are complicated by destannylation to the tricyclic iodide 14. However, after hydrogenation, treatment with 1 mol equivalent of iodine gives the tin iodide 17 which is reduced to the tin hydride 18. The hydroxyalkyltin hydride 21 is similarly prepared. The unsaturated tin hydrides 24 and 26 have been prepared by reduction of the Diels–Alder adducts 23 and 25 obtained from cyclopentadiene and methyl (Z )-3-(chlorodiphenylstannyl)acrylate. The tin hydrides 18 and 21 are found to undergo free-radical reactions as exemplified by addition to methyl propiolate and reductive dehalogenation of the iodo lactone 30.

References

1. M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987.
2. A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini and A. Umani-Ronchi, J. Am. Chem. Soc., 1993, 115, 7001; G. E. Keck, K. H. Tarbet and L. S. Geraci, J. Am. Chem. Soc., 1993, 115, 8467; S. Aoki, K. Mikami, M. Terada and T. Nakai, Tetrahedron, 1993, 49, 1783; G. E. Keck, D. Krishnamurthy and M. C. Grier, J. Org. Chem., 1993, 58, 6543; G. E. Keck and L. S. Geraci, Tetrahedron Lett., 1993, 34, 7827; G. E. Keck, D. Krishnamurthy and X. Chen, Tetrahedron Lett., 1994, 35, 8323; A. Yanagisawa, H. Nakashima, A. Ishiba and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 4723; J. W. Faller, D. W. Sams and X. Liu, J. Am. Chem. Soc., 1996, 118, 1217; C.-M. Yu, H.-S. Choi, W.-H. Jung, H.-J. Kim and J. Shin, Chem. Commun., 1997, 761; A. Yanagisawa, A. Ishiba, H. Nakashima and H. Yamamoto, Synlett, 1997, 88; P. G. Cozzi, P. Orioli, E. Tagliavini and A. Umani-Ronchi, Tetrahedron Lett., 1997, 38, 145; J. A. Marshall and Y. Tang, Synlett, 1992, 653.
3. S. Kobayashi and T. Mukaiyama, Chem. Lett., 1989, 297; T. Mukaiyama, H. Uchiro and S. Kobayashi, Chem. Lett., 1989, 1001; T. Mukaiyama, H. Uchiro and S. Kobayashi, Chem. Lett., 1989, 1757; T. Mukaiyama, S. Kobayashi and T. Sano, Tetrahedron, 1990, 46, 4653; S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; T. Mukaiyama, H. Uchiro, I. Shiina and S. Kobayashi, Chem. Lett., 1990, 1019; T. Mukaiyama, I. Shiina and S. Kobayashi, Chem. Lett., 1991, 1901; S. Kobayashi, Y. Fujishita and T. Mukaiyama, Chem. Lett., 1990, 1455; S. Kobayashi, M. Furuya, A. Ohtsubo and T. Mukaiyama, Tetrahedron: Asymmetry, 1991, 2, 635; T. Mukaiyama, S. Kobayashi, H. Uchiro and I. Shiina, Chem. Lett., 1990, 129; T. Mukaiyama, M. Furuya, A. Ohtsubo and S. Kobayashi, Chem. Lett., 1991, 989; S. Kobayashi, H. Uchiro, I. Shiina and T. Mukaiyama, Tetrahedron, 1993, 49, 1761; S. Kobayashi, A. Ohtsubo and T. Mukaiyama, Chem. Lett., 1991, 831; S. Kobayashi and T. Kawasuji, Synlett, 1993, 911.
4. R. Krishnamurti and H. G. Kuivila, J. Org. Chem., 1986, 51, 4947; D. Young, M. Jones and W. Kitching, Aust. J. Chem., 1986, 563.
5. U.-M. Gross, M. Bartels and D. Kaufmann, J. Organomet. Chem., 1988, 344, 277; J. M. Chong, G. K. MacDonald, S. B. Park and S. H. Wilkinson, J. Org. Chem., 1993, 58, 1266.
6. D. Nanni and D. Curran, Tetrahedron: Asymmetry, 1996, 7, 2417; M. Blumenstein, K. Schwarzkopf and J. O. Metzger, Angew. Chem., Int. Ed. Engl., 1997, 36, 235.
7. H. Schumann and B. C. Wassermann, J. Organomet. Chem., 1989, 365, C1.
8. H. Schumann, B. C. Wassermann and J. Pickardt, Organometallics, 1993, 12, 3051.
9. H. Schumann, B. C. Wassermann and F. E. Hahn, Organometallics, 1992, 11, 2803.
10. J. C. Podesta, A. B. Chopa, G. E. Radivoy and C. A. Vitale, J. Organomet. Chem., 1995, 494, 11; C. A. Vitale and J. C. Podesta, J. Chem. Soc., Perkin Trans. 1, 1996, 2407.
11. J. Otera, Y. Yoshinaga, T. Yamaji, T. Yoshioka and Y. Kawasaki, Organometallics, 1985, 4, 1213.
12. P. J. Cox, S. M. S. V. Doidge-Harrison, R. A. Howie, I. W. Nowell, O. J. Taylor and J. W. Wardell, J. Chem. Soc., Perkin Trans. 1, 1989, 2017; O. J. Taylor and J. L. Wardell, Recl. Trav. Chim. Pays-Bas, 1988, 107, 267; L. D. Hall, P. R. Steiner and D. C. Miller, Can. J. Chem., 1978, 57, 38; K. J. Hale, L. Hough and A. C. Richardson, Carbohydr. Res., 1988, 177, 259.
13. H. C. Brown and K. S. Bhat, J. Am. Chem. Soc., 1986, 108, 293, 5919; H. C. Brown and P. K. Jadhav, J. Org. Chem., 1984, 49, 4089; H. C. Brown and N. N. Joshi, J. Org. Chem., 1988, 53, 4059.
14. C. R. Johnson and J. F. Kadow, J. Org. Chem., 1987, 52, 1493.
15. M. Gielen, Top. Curr. Chem., 1982, 104, 57; G. J. D. Peddle and G. Redl, J. Chem. Soc., Chem. Commun., 1968, 626; M. Gielen, Top. Stereochem., 1980, 12, 217; M. Gielen and Y. Tondeur, J. Organomet. Chem., 1979, 169, 265.
16. J. K. Stille and B. L. Groh, J. Am. Chem. Soc., 1987, 109, 813.
17. J. C. Cochran, L. E. Williams, B. S. Bronk, J. A. Calhoun, J. Fassberg and K. G. Clark, Organometallics, 1989, 8, 804.
18. K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923.
19. H. X. Zhang, F. Guibe and G. Balavoine, J. Org. Chem., 1990, 55, 1857; Y. Ichinose, H. Oda, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1987, 60, 3468; H. Miyake and K. Yamamura, Chem. Lett., 1989, 981; J. C. Cochran, B. S. Bronk, K. M. Terrence and H. K. Phillips, Tetrahedron Lett., 1990, 31, 6621.
20. E. Piers, J. M. Chong and H. E. Morton, Tetrahedron, 1989, 45, 363; E. Piers, T. Wong and K. A. Ellis, Can. J. Chem., 1992, 70, 2058.
21. L. M. Jackman and S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd edn., Pergamon, 1969, p. 84.
22. I. Fleming and C. Urch, Tetrahedron Lett., 1983, 24, 4591; J. F. Kadow and C. R. Johnson, Tetrahedron Lett., 1984, 25, 5255; J. W. Herndon and J. J. Harp, J. Organomet. Chem., 1990, 393, C1; G. E. Keck and S. D. Tonnies, Tetrahedron Lett., 1993, 34, 4607.
23. Y. Yamamoto and A. Yanagi, Chem. Pharm. Bull., 1982, 30, 1731.
24. H. G. Kuivila, Synthesis, 1970, 499.
25. W. P. Neumann and J. Pedain, Tetrahedron Lett., 1964, 2461.
26. M. Ochiai, S. Iwaki, T. Ukita, Y. Mitsuura, M. Shiro and Y. Nagao, J. Am. Chem. Soc., 1988, 110, 4606.
27. F. B. Gonzales and P. A. Bartlett, Org. Synth., 1990, Coll. Vol. VII, 164.
28. K. Miura, Y. Ichinose, K. Nozaki, F. Fugami, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1989, 62, 143.
29. E. J. Corey and J. W. Suggs, J. Org. Chem., 1975, 44, 2554.
30. R. Beddoes, R. M. Pratt and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1998, 717.