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Stereocontrolled intramolecular nitrile oxide cycloaddition reaction using a gauche-gauche interaction |
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| Authors: | Michihiko Noguchi Aiko Tsukimoto Jun Hikata |
| Institution: | a Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Tokiwadai, Ube 755-8611, Japan b Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan |
| Abstract: | A gauche-gauche interaction is proposed as a powerful controlling factor for the stereochemistry in the intramolecular nitrile oxide cycloaddition reaction derived from N-protected 3-(N-allylamino)propionaldehyde and 2-(N-homoallylamino)acetaldehyde oximes. High levels of stereoselectivity (76% de to perfect) were obtained from the reaction involving nitrile oxides with substituents at the adjacent carbon atom to the tether nitrogen. |
| Keywords: | Stereocontrol Gauche-gauche interaction Intramolecular nitrile oxide cycloaddition |
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