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Unexpected 1,2 syn diastereoselectivity in the three-component ‘aza Sakurai-Hosomi’ reaction
Authors:Jean-René   Ella-Menye,André   Mann
Affiliation:Laboratoire de Pharmacochimie de la Communication Cellulaire, UMR 7081, Faculté de Pharmacie, 74, route du Rhin, BP 60024, F-67401 Illkirch, France
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.
Keywords:Sakurai-Hosomi reaction   Three-component reaction   Allylsilane   Homoallylamine   Diastereoselectivity
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