Dieter R Karl, Gore Vinayak K, Chen Ningyi
Howard L. Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, SC 29634-1905, USA.
Org Lett. 2004 Mar 4;6(5):763-6. doi: 10.1021/ol0364576.
Alpha-(N-carbamoyl)alkylcuprates (RCuCNLi or R2CuLi) react with allylic phosphates to afford homoallylic amines in good chemical yields. Regioselectivity is governed by steric factors in both the cuprate reagent and phosphate substrate and systems can be designed to give either the S(N)2' or S(N)2 substitution product cleanly. Excellent enantioselectivities can be achieved with either a scalemic alpha-di[(N-carbamoyl)alkyl]cuprate and an achiral phosphate or with a scalemic allylic phosphate and an achiral cuprate reagent. [reaction: see text]
α-（N-甲酰基）烷基铜酸盐（RCuCNLi或R2CuLi）与烯丙基磷酸酯反应，以良好的化学产率得到高烯丙基胺。区域选择性受铜酸盐试剂和磷酸酯底物中的空间因素控制，并且可以设计体系以干净地给出S(N)2'或S(N)2取代产物。使用非对映体纯的α-二[（N-甲酰基）烷基]铜酸盐和非手性磷酸酯，或者使用非对映体纯的烯丙基磷酸酯和非手性铜酸盐试剂，都可以实现优异的对映选择性。[反应：见正文]
