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