In the [3 + 2] cycloaddition of a range of nitrile oxides with homochiral vinyl ethers the diastereoselectivity observed is dependent on the chiral auxiliary used; an X-ray structure determination of the major isomer of product 11a, from the reaction of benzonitrile oxide and (S)-1-(2-naphthyl)ethyl vinyl ether, is consistent with the proposed preferred conformation of the vinyl ether.
A. N. Boa, S. E. Booth, D. A. Dawkins, P. R. Jenkins, J. Fawcett and D. R. Russell, J. Chem. Soc., Perkin Trans. 1, 1993, 1277 DOI: 10.1039/P19930001277
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