Asymmetric Synthesis of Nonracemic Primary Amines via Spiroborate-Catalyzed Reduction of Pure (E)-and (Z)-O-Benzyloximes: Applications toward the Synthesis of …

…, KM Santiago, M Ortiz-Marciales

Index: Ou, Wenhua; Espinosa, Sandraliz; Melendez, Hector J.; Farre, Silvia M.; Alvarez, Jaime L.; Torres, Valerie; Martinez, Ileanne; Santiago, Kiara M.; Ortiz-Marciales, Margarita Journal of Organic Chemistry, 2013 , vol. 78, # 11 p. 5314 - 5327

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Citation Number: 6

Abstract

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 ...