Tetrahedron Letters p. 2637 - 2638 (1991)
Update date:2022-08-04
Topics:
Lambs, Laurent
Singh, Narrinder P.
Biellmann, Jean-Francois
The 1,4 addition of the anion of allylphenylthioether to 3,3-dimethylacrylonitrile occurred in 76% at the α position to the sulfur. The allylic alcohol 5 obtained from thioether 3 was asymetrically epoxidised with the Katsuki-Sharpless procedure to [4S,5R] epoxyalcohol 6 (ee> 94%). The silyl ether 8 was cyclised to the cis and trans nitrile 9. Cleavage of the glycol 10 gave the cis 11 and trans-aldehyde 12. Later 12 was converted to [1R,3R] trans chrysanthemic nitrile 13 (ee 92%).
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(1991)
