Tetrahedron Asymmetry p. 955 - 965 (1998)
Update date:2022-08-05
Topics:
Garcia-Martinez, Cirilo
Taguchi, Yoichi
Oishi, Akihiro
Hayamizu, Kikuko
The ring current effects of the phenyl and 1-naphthyl rings are used to determine the absolute configuration of ten chiral azetidinones prepared from the [2+2] cycloaddition of (S)-1-(1-naphthyl)ethyl and (S)-1-phenylethyl isocyanate to vinyl ethers under high pressure. The (S)-1-arylethyl group of the studied azetidinones adopts a preferred conformation that can be distinguished by 1H NMR spectroscopy. The application of this principle to other azetidinones containing the arylethyl substituent is consistent with the configurations determined by chemical correlation and X-ray diffraction and verifies the reliability of the proposed method.
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