Use of the bifunctional reagent (Z)-4-iodo-1-(tributylstannyl)but-1-ene: A new cyclohexenone annulation method

Synlett

Volumn , Issue 5, 1998, Pages 516-518

  Piers, Edward ^a   Boulet, Serge L ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002677807     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1707     Document Type: Article

References (24)

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4. Larock, R. C. Comprehensive Organic Transformations; VCH Publishers: New York, 1989; pp. 668-672.
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8. All new, fully characterized compounds reported herein exhibit spectra in accord with structural assignments and gave satisfactory elemental analyses and high resolution mass spectrometric molecular mass determinations.
9. Barbero, A.; Cuadrado, P.; Fleming, I.; González, A. M.; Pulido, F. J.; Rubio, R. J. Chem. Soc. Perkin Trans 1 1993, 1657.
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13. Bergbreiter, D. E.; Momongan, M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Heathcock, C. H., Ed.; pp. 503-525.
14. Attempts to alkylate ketone enolates with the iodide 6 resulted primarily in elimination of HI from the homoallylic electrophile. This problem was circumvented by the use of the dimethylhydrazone derivatives.
15. Piers, E.; Coish, P. D. Synthesis 1995, 47, and citations therein.
16. Corey, E. J.; Pearce, H. L. J. Am. Chem. Soc. 1979, 101, 5841.
17. Piers, E.; Cook, K. L.; Rogers, C. Tetrahedron Lett. 1994, 35, 8573.
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19. Cheng, Y.-S.; Liu, W.-L.; Chen, S. Synthesis 1980, 223.
20. Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682.
21. Cf. Piers, E.; Friesen, R. W.; Keay, B. A. Tetrahedron 1991, 47, 4555.
22. On the basis of examination of molecular models, it seems likely that cyclization of the organolithium intermediate derived from 16 would occur via attack on the carbonyl carbon from the side opposite to the adjacent methyl group. Thus, although the relative configuration of 17 was not rigorously established, one would predict a cis ring fusion.
23. These isomers, produced in a ratio of approximately 2.5:1, were chromatographically separated and individually characterized.
24. This issue will be discussed in detail in a full account of this work.