134812-56-9Relevant academic research and scientific papers
Enantiospecific synthesis of a chrysanthemic acid precursor by the Katsuki-Sharpless epoxidation and the stork cyclisation
Lambs, Laurent,Singh, Narrinder P.,Biellmann, Jean-Francois
, p. 2637 - 2638 (1991)
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%).
