Stereoselective Conjugate Addition of Lithium (Phenylthio)(trimethylstannyl)cuprate to, α,β-Acetylenic Esters. Preparation of (E)- and (Z)-4-Lithio-l,3-pentadienes and Their Reaction with Electrophiles

Journal of Organic Chemistry

Volumn 45, Issue 21, 1980, Pages 4263-4264

  Piers, Edward ^a   Morton, Howard E ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000244684     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01309a053     Document Type: Article

References (13)

1. Posner, G. H.; Brunelle, D. J.; Sinoway, L. Synthesis 1974, 662.
2. Still, W. C. J. Am. Chem. Soc. 1977, 99, 4836.
3. Piers, E.; Morton, E. J. Chem. Soc., Chem. Commun. 1978, 1033.
4. Piers, E.; Nagakura, I. Synth. Commun. 1975, 5, 193.
5. Piers, E.; Morton, H. E. J. Org. Chem. 1979, 44, 3437.
6. Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969,91, 1851.
7. Siddall, J. B.; Biskup, M.; Fried, J. H. J. Am. Chem. Soc. 1969, 91, 1853.
8. Wollenberg, R. H. Tetrahedron Lett. 1978, 717.
9. Chen, S. L.; Schaub, R. E.; Grudzinskas, C. V. J. Org. Chem. 1978, 43, 3450.
10. Collins, P. W.; Jung, C. J.; Gasiecki, A.; Pappo, R. Tetrahedron Lett. 1978, 3187.
11. Firouzabadi, H.; Ghaderi, E. Tetrahedron Lett. 1978, 839.
12. For a stimulating review on methods of reactivity umpolung, see: Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
13. For some recent examples of reagents corresponding to similar d3 synthons, see ref 14c and: Posner, G. H.; Ting, J.-S.; Lentz, C. M. Tetrahedron 1976, 32, 2281; Corey, E. J.; Wollenberg, R. H. Tetrahedron Lett. 1976, 4705; Corey, E. J.; Bock, M. G.; Kozikowski, A. P.; Rama Rao, A. V.; Floyd, D.; Lipshutz, B. Angew. Chem., Int. Ed. Engl. 1978, 1051.