New Bifunctional Reagents: 2-(Trimethylgermyl)allylcopper(I)-dimethyl sulfide and 2-(Trimethylstannyl)allylcopper(I)-dimethyl sulfide and their Conjugate Addition to α,β-Unsaturated Ketones

Synlett

Volumn 1996, Issue 6, 1996, Pages 549-552

  Piers, Edward ^a   Kaller, Alan Matthew ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038246056     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5492     Document Type: Article

References (27)

1. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135, and references cited therein.
2. Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Smith, R. A. J. J. Am. Chem. Soc. 1990, 112, 4404.
3. Lipshutz, B. H.; Ung, C.; Ellsworth, T. R.; Reuter, D. C. Tetrahedron Lett. 1990, 31, 4539.
4. Lipshutz, B. H.; Hackmann, C. J. Org. Chem. 1994, 59, 7437.
5. For examples of allylcopper(I) reagents with substitution in the 1-position see: Corriu, R. J. P.; Guerin, C.; M'Boula, J. Tetrahedron Lett. 1981, 22, 2985. Hojo, M.; Harada, H.; Murakami, C.; Hosomi, A. J. Chem. Soc., Chem. Commun. 1994, 2687.
6. For examples of allylcopper(I) reagents with substitution in the 1-position see: Corriu, R. J. P.; Guerin, C.; M'Boula, J. Tetrahedron Lett. 1981, 22, 2985. Hojo, M.; Harada, H.; Murakami, C.; Hosomi, A. J. Chem. Soc., Chem. Commun. 1994, 2687.
7. For recent papers, see Piers, E.; Cook, K. L.; Rogers, C. Tetrahedron Lett. 1994, 35, 8573; Piers, E.; Lemieux, R. J. Chem. Soc. Perkin Trans. 1 1995, 3; Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem., 1995, 60, 2322; Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857.
8. For recent papers, see Piers, E.; Cook, K. L.; Rogers, C. Tetrahedron Lett. 1994, 35, 8573; Piers, E.; Lemieux, R. J. Chem. Soc. Perkin Trans. 1 1995, 3; Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem., 1995, 60, 2322; Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857.
9. For recent papers, see Piers, E.; Cook, K. L.; Rogers, C. Tetrahedron Lett. 1994, 35, 8573; Piers, E.; Lemieux, R. J. Chem. Soc. Perkin Trans. 1 1995, 3; Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem., 1995, 60, 2322; Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857.
10. For recent papers, see Piers, E.; Cook, K. L.; Rogers, C. Tetrahedron Lett. 1994, 35, 8573; Piers, E.; Lemieux, R. J. Chem. Soc. Perkin Trans. 1 1995, 3; Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem., 1995, 60, 2322; Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857.
11. This material was readily obtained by treatment of commercially available 2,3-dibromopropene with aqueous potassium carbonate at 90°C. See Hatch, L. F.; Alexander, H. E.; Randolph, J. D. J. Org. Chem. 1950, 15, 654.
12. Corey, E. J.; Widiger, G. N. J. Org. Chem. 1975, 40, 2975.
13. All compounds reported herein exhibit spectra in accord with structural assignments and new compounds gave satisfactory elemental analyses and (or) high resolution mass spectrometric molecular mass determinations.
14. Lipshutz, B. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 4617.
15. Reimann, W.; Kuivila, H. G.; Farah, D.; Apoussidis, T. Organometallics 1987, 6, 557; Still, W. C. J. Am. Chem. Soc. 1978, 700, 1481.
16. Reimann, W.; Kuivila, H. G.; Farah, D.; Apoussidis, T. Organometallics 1987, 6, 557; Still, W. C. J. Am. Chem. Soc. 1978, 700, 1481.
17. Still, W. C. J. Am. Chem. Soc. 1977, 99, 4836.
18. Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079.
19. Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969.
20. For generation of other allyltrialkylstannanes substituted in the 2-position and unsuccessful attempts at conjugate additions of reagents derived therefrom, see Overman, L. E.; Renhowe, P. A. J. Org. Chem. 1994, 59, 4138; Lee, E.; Yu, S.-G.; Hur, C-U.; Yang, S.-M. Tetrahedron Lett. 1988, 29, 6969; Fleming, I.; Rowley, M. Tetrahedron 1989, 45, 413; Barbero, A.; Cuadrado, P.; Fleming, I.; González, A. M.; Pulido, F. J. J. Chem. Soc. Perkin Trans. 1 1992, 327.
21. For generation of other allyltrialkylstannanes substituted in the 2-position and unsuccessful attempts at conjugate additions of reagents derived therefrom, see Overman, L. E.; Renhowe, P. A. J. Org. Chem. 1994, 59, 4138; Lee, E.; Yu, S.-G.; Hur, C-U.; Yang, S.-M. Tetrahedron Lett. 1988, 29, 6969; Fleming, I.; Rowley, M. Tetrahedron 1989, 45, 413; Barbero, A.; Cuadrado, P.; Fleming, I.; González, A. M.; Pulido, F. J. J. Chem. Soc. Perkin Trans. 1 1992, 327.
22. For generation of other allyltrialkylstannanes substituted in the 2-position and unsuccessful attempts at conjugate additions of reagents derived therefrom, see Overman, L. E.; Renhowe, P. A. J. Org. Chem. 1994, 59, 4138; Lee, E.; Yu, S.-G.; Hur, C-U.; Yang, S.-M. Tetrahedron Lett. 1988, 29, 6969; Fleming, I.; Rowley, M. Tetrahedron 1989, 45, 413; Barbero, A.; Cuadrado, P.; Fleming, I.; González, A. M.; Pulido, F. J. J. Chem. Soc. Perkin Trans. 1 1992, 327.
23. For generation of other allyltrialkylstannanes substituted in the 2-position and unsuccessful attempts at conjugate additions of reagents derived therefrom, see Overman, L. E.; Renhowe, P. A. J. Org. Chem. 1994, 59, 4138; Lee, E.; Yu, S.-G.; Hur, C-U.; Yang, S.-M. Tetrahedron Lett. 1988, 29, 6969; Fleming, I.; Rowley, M. Tetrahedron 1989, 45, 413; Barbero, A.; Cuadrado, P.; Fleming, I.; González, A. M.; Pulido, F. J. J. Chem. Soc. Perkin Trans. 1 1992, 327.
24. House, H. O.; Chu, C-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem. 1975, 40, 1460; Wuts, P. G. M. Synth. Commun. 1981, 11, 139.
25. House, H. O.; Chu, C-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem. 1975, 40, 1460; Wuts, P. G. M. Synth. Commun. 1981, 11, 139.
26. 2S complex in THF and, hence, a more rapid formation of the required allylcopper(I) reagent 2.
27. 3SiBr in promoting conjugate addition of organocopper(I) reagents to enones has been noted previously: Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857, and references given therein. In the current study, the use of other additives was not examined.