Abstract
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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