Conjugate addition of α-alkoxystannanes via in situ transmetalation using catalytic CuCN

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3811-3814

  Bhatt, Rama K ^a   Ye, Jianhua ^a   Falck, J R ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; ORGANIC CHEMISTRY;

EID: 0029936142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00710-1     Document Type: Article

References (22)

1. Review: Lipshutz, B.H.; Sengupta, S. Org. Reactions 1992, 41, 135-631.
2. Falck, J.R.; Bhatt, R.K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982. Also see, Ye, J.; Bhatt, R.K.; Falck, J. J. Am. Chem. Soc. 1994, 116, 1-5.
3. Falck, J.R.; Bhatt, R.K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982. Also see, Ye, J.; Bhatt, R.K.; Falck, J. J. Am. Chem. Soc. 1994, 116, 1-5.
4. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L.S. J. Org. Chem. 1994, 59, 5905-5911 and cited references.
5. For an example of transmetalation between vinylstannanes and higher order cyanocuprates see, Behling, J.R.; Babiak, K.A.; Ng, J.S.; Campbell, A.L.; Moretti, R.; Koerner, M.; Lipshutz, B.H. J. Am. Chem. Soc. 1988, 110, 2641-2643.
6. The CuCl-mediated conjugate addition of vinyltrimethylstannanes to α,β-unsaturated carbonyls has been reported: Piers, E.; McEachern, E.J.; Burns, P.A. J. Org. Chem. 1995, 60, 2322-2323. Tanaka, H.; Kameyama, J.; Sumida, S.-i.; Torii, S. Tetrahedron Lett, 1992, 33, 7029-7030.
7. The CuCl-mediated conjugate addition of vinyltrimethylstannanes to α,β-unsaturated carbonyls has been reported: Piers, E.; McEachern, E.J.; Burns, P.A. J. Org. Chem. 1995, 60, 2322-2323. Tanaka, H.; Kameyama, J.; Sumida, S.-i.; Torii, S. Tetrahedron Lett, 1992, 33, 7029-7030.
8. α-Alkoxyorganocuprates generated by conventional methodology undergo conjugate additions: Linderman, R.J.; Godfrey, A. Tetrahedron Lett. 1986, 27, 4553-4556.
9. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
10. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
11. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
12. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
13. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
14. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
15. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
16. Linderman, R.J.; Godfrey, A.; Horne, K. ibid. 1987, 28, 3911-3914. Hutchinson, D.K.; Fuchs, P.L. J. Am. Chem. Soc. 1987, 109, 4930-4939. Linderman, R.J.; Godfrey, A. ibid. 1988, 110, 6249-6251. Linderman, R.J.; Godfrey, A.; Horne, K. Tetrahedron 1989, 45, 495-506. Knochel, P.; Chou, H.G.C.; Yeh, M.C.P.; Rozema, M.J. J. Org. Chem. 1989, 54, 5202-5204. Knochel, P.; Chou, T.-S. J. Org. Chem. 1990, 55, 4791. Linderman, R.J.; Griedel, B.D. ibid. 1990, 55, 5428-5432. Linderman, R.J.; Griedel, B.D. ibid. 1991, 56, 5491-5493.
17. 13C, MS) were obtained for all new compounds.
18. 2SiCl, and AcCl, gave little or no adduct.
19. Piers, E.; McEachem, E.J.; Romero, M.A. Tetrahedron Lett. 1996, 37, 1173-1176.
20. Clive, D.L.J.; Cheshire, D.R.; Set, L. J. Chem. Soc., Chem. Comm. 1987, 353-355.
21. While quaternary α-hydroxystannanes are readily available from addition of lithium stannyl anions to ketones, the adducts can not be converted to α-thionocarbamoyl stannanes in preparative useful yields.
22. Conjugate addition to allylic epoxides by organocopper reagents is well known: Anderson, R.J. J. Am. Chem. Soc. 1970, 92, 4978-4979.