用于合成2-氨基茚满衍生物的不对称钯催化烯烃碳胺化反应
Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.
作者信息
White Derick R, Hutt Johnathon T, Wolfe John P
机构信息
Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
出版信息
J Am Chem Soc. 2015 Sep 9;137(35):11246-9. doi: 10.1021/jacs.5b07203. Epub 2015 Aug 27.
Abstract
A new type of Pd-catalyzed alkene carboamination reaction that provides direct access to enantioenriched 2-aminoindanes from 2-allylphenyltriflate derivatives and aliphatic amines is described. A catalyst generated in situ from Pd(OAc)2 and (S)-tert-butylPHOX provides the functionalized carbocycles in good yield with up to >99:1 er. The transformations occur via a key anti-aminopalladation that involves intermolecular attack of an amine nucleophile on an arylpalladium alkene complex.
摘要
描述了一种新型的钯催化烯烃碳胺化反应，该反应可从2-烯丙基苯基三氟甲磺酸酯衍生物和脂肪族胺直接获得对映体富集的2-氨基茚满。由醋酸钯和（S）-叔丁基PHOX原位生成的催化剂能以良好的产率提供功能化的碳环，对映体过量比高达>99:1。该转化过程通过关键的反式氨基钯化反应进行，其中涉及胺亲核试剂对芳基钯烯烃络合物的分子间进攻。
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