Stereoselective [2,3]-Wittig and tandem [2,3]-Wittig-anionic oxy-Cope rearrangements of bis-allylic ethers: Effect of substituents

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6445-6448

  Greeves, Nicholas ^a   Lee, Wai Man ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; POLYENE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

OXY;

EID: 0030753377     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01473-1     Document Type: Article

References (19)

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2. Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885-902, Nakai, T.; Mikami, K. Org. React., 1994, 46, 105-209.
3. Marshall, J. A. Comprehensive Organic Synthesis; B. M. Trost, Ed.; Pergamon: 1991; Vol. 3. pp975-1014
4. Wilson, S. R. Organic Reactions; Paquette, L. A. Ed.; John Wiley & Sons Inc.: New York, 1993; Vol. 43; pp 93-251.
5. Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S.; Yun, J. S. J. Org. Chem., 1994, 59, 1444-1456.
6. Paquette, L. A.; Liang, S.; Wang, H-L. J. Org. Chem., 1996, 61, 3268-3279.
7. Hill, R. K. Comprehensive Organic Synthesis; B. M. Trost, Ed.; Pergamon: 1991; Vol. 5; pp785-826.
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11. Greeves, N.; Vines, K. J. J. Chem. Soc., Chem Commun., 1994, 1469-1470.
12. Greeves, N.; Vines, K. J. Tetrahedron Lett., 1994, 35, 7077-7080.
13. b, have been found to be 1.0-1.5 Hz higher than corresponding coupling in the syn isomers. Similar results have been observed previously by Tsai, D. S. J.; Midland, M. M. J. Org. Chem., 1984, 49, 1842-1843.
14. Nakai, T.; Mikami, K. J. Synthesis, 1991, 594-604.
15. Gajewski, J. J.; Gee, K. R. J. Am. Chem. Soc., 1991, 113, 967-971.
16. 1H NMR analysis. An additional olefinic proton signal appeared as triplet doublet at δ 6.3 (td, J = 6.6 and 1.6 Hz) and the aldehyde proton was shifted from the usual δ 9.7 (t, J = 2.2 Hz) to δ 9.2 (d, J = 1.1 Hz) and displayed reduced multiplicity.
17. Paquette, L. A. Angew. Chem. Int. Ed. Engl., 1990, 29, 609-626.
18. Following papers in this issue, Greeves, N.; Lee, W. M. Tetrahedron Lett., 1997, 38, 6449 and Greeves, N.; Lee, W. M., Barkley, J. V. Tetrahedron Lett., 1997, 38, 6453.
19. Following papers in this issue, Greeves, N.; Lee, W. M. Tetrahedron Lett., 1997, 38, 6449 and Greeves, N.; Lee, W. M., Barkley, J. V. Tetrahedron Lett., 1997, 38, 6453.