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以(+)-樟脑缩苄胺作中间体对映选择合成(R)-α-取代苄胺

Enantioselective Synthesis of (R)-α-Substituted Benzyl Amines Using (+)-Camphor Imine of Benzyl Amine as Intermediate
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摘要 本文报道以(+)-樟脑作手性助剂,苄胺为原料,二者缩合制得的酮亚胺作中间体3,不对称合成(R)-α-取代苄胺(7)的一条有效新途径。化合物3用丁基锂去质子化提供的锂衍生物4和卤代烷反应,以较高立体选择性产生烷基化产物6,化合物6用醋酸羟胺转氨反应后,获得了光学产率为4.6-90%的(R)-α-取代苄胺(7),以肟的形式回收(+)-樟脑。 A new and efficient asymmetrically synthetic route of (R)-α-substituted benzyl amines 7 via ketimine intermediate 3, usiug (+)-camphor as chiral auxilliary reagent and benzylamine as starting material, has been reported. Deprotonation of compound 3 with butyllithium affords 4, which reacted with alkyl halides be give the alkylated products 6 with high diastereoselectivity. After transamination of compounds 6 with hydroxylamine acetate the (R)-α-substituted banzyl amines 7 in optical purity of 4.6-- 90% are obtained and (+)-camphor is recovered as its oxime.
出处 《化学学报》 SCIE CAS CSCD 北大核心 1989年第7期662-667,共6页 Acta Chimica Sinica
基金 中国科学院科学基金
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