Stereoselective synthesis of homoallylic alcohols by migratory insertion reactions of higher-order cyanocuprates and nickel-catalysed coupling reactions involving enol carbamates

Synlett

Volumn 1989, Issue 1, 1989, Pages 52-54

  Kocienski, Philip ^a   Dixon, Nicholas J ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85032754032     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1989-34703     Document Type: Article

References (17)

1. Wadman, S.; Whitby, R.; Yeates, G; Kocienski, P.; Cooper, K. J. Chem. Soc., Chem. Common. 1987, 241.
2. Kocienski, P.; Dixon, N. J.; Wadman, S. Tetrahedron Lett. 1988, 29, 2353.
3. Kocienski, P.; Wadman, S.; Cooper, K. Tetrahedron Lett. 1988, 29, 2357.
4. Kocienski, P.; Love, C; Whitby, R.; Roberts, D. A. Tetrahedron Lett. 1988, 29, 2867.
5. Kocienski, P; Wadman, S.; and Cooper, K. J. Am. Chem. Soc 1989, 111, 2363.
6. Review of cyanocuprate chemistry: Lipshutz, B. H. Synthesis 1987, 325.
7. Migratory insertion reactions of the type reported herein represent a new and powerful class of reactions for the metal-mediated synthesis of C-C bonds. For other recent contributions, see: Negishi, E.; Akiyoshi, K. J. Am. Chem. Soc 1988, 110, 646.
8. Negishi, E.; Akiyoshi, K.; O'Connor, B.; Takagi, K.; Wu, G. J. Am. Chem. Soc 1989, 111, 1125.
9. Erdelmeier, I.; Gais, H.-J J. Am. Chem. Soc 1989, 111, 1125.
10. Review: Hoppe, D. Angew. Chem. 1984, 96, 930;
11. Angew. Chem., Int. Ed. Engl 1984, 23, 932.
12. Kramer, T.; Hoppe, D. Tetrahedron Lett. 1987, 28, 5149.
13. Hoppe, D.; Krämer, T. Angew. Chem. 1986, 98, 171;
14. Angew. Chem., Int. Ed. Engl 1986, 25, 160.
15. The formation of acetylene 18 from metalated enol carbamate 13 may be an example of a Fritsch-Buttenberg- Wiechell rearrangement: Kobrich, E. Angew. Chem. 1965, 77, 75;
16. Angew. Chem., Int. Ed. Engl 1965, 4, 49.
17. For the transmetalation between alkenylstannanes 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.