Tetrahedron letters

Enantiospecific synthesis of a chrysanthemic acid precursor by the Katsuki-Sharpless epoxidation and the stork cyclisation

L Lambs, NP Singh, JF Biellmann

Index: Lambs, Laurent; Singh, Narrinder P.; Biellmann, Jean-Francois Tetrahedron Letters, 1991 , vol. 32, # 23 p. 2637 - 2638

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Citation Number: 7

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 obtained from thioether was asymetrically epoxidised with the Katsuki-Sharpless procedure to [4S,5R] epoxyalcohol (ee > 94%). The silyl ether was cyclised to the cis and trans nitrile . Cleavage of the glycol gave the cis and trans-aldehyde . Later was converted to [1R,3R] trans chrysanthemic nitrile (ee 92%).