Unexpected 1,2 syn diastereoselectivity in the three-component ‘aza Sakurai-Hosomi’ reaction |
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| Authors: | Jean-René Ella-Menye,André Mann |
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| Affiliation: | Laboratoire de Pharmacochimie de la Communication Cellulaire, UMR 7081, Faculté de Pharmacie, 74, route du Rhin, BP 60024, F-67401 Illkirch, France |
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| Abstract: | The three-component ‘aza Sakurai-Hosomi’ reaction performed on (±) O-protected mandelic aldehydes provided the unexpected syn hydroxy homoallylamines 2 and 2d as the major adducts. An intramolecular chelated transition state via a hydrogen bond is proposed to explain this 1,2 syn diastereoselectivity. |
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| Keywords: | Sakurai-Hosomi reaction Three-component reaction Allylsilane Homoallylamine Diastereoselectivity |
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