Asymmetric Synthesis of Nonracemic Primary Amines via Spiroborate-Catalyzed Reduction of Pure (E)- and (Z)-O-Benzyloximes: Applications toward the Synthesis of Calcimimetic Agents
2013
Ou, Wenhua | Espinosa, Sandraliz | Meléndez, Héctor J. | Farré, Silvia M. | Alvarez, Jaime L. | Torres, Valerie | Martínez, Ileanne | Santiago, Kiara M. | Ortiz-Marciales, Margarita
Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst. Two convenient and facile approaches to the synthesis of new and known calcimimetic analogues employing enantiopure (1-naphthalen-1-yl)ethylamine as chiral precursor are described.
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