通过亲核β-丙氨酸等价物的二烷基化反应高效合成对称的α,α-二取代β-氨基酸和α,α-二取代醛。

Efficient synthesis of symmetrical alpha,alpha-disubstituted beta-amino acids and alpha,alpha-disubstituted aldehydes via dialkylation of nucleophilic beta-alanine equivalent.

机构信息

The Center for Drug Discovery and Design, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.

出版信息

J Org Chem. 2010 Mar 5;75(5):1717-22. doi: 10.1021/jo902699t.

DOI:10.1021/jo902699t

Abstract

Homologation of the nucleophilic beta-alanine equivalent beta-Ala Ni(II)-PABP [Ni(II) complex of beta-alanine Schiff base with 2-[N-(alpha-picolyl)amino]benzophenone (PABP), 1] via alkyl halide alkylation was systematically studied as a general method for preparing symmetrically alpha,alpha-disubstituted beta-amino acids. The dialkylation reactions could be easily performed and did not require inert atmosphere, dried solvents, and low temperatures, thereby affording the benefits of operationally convenient experimental procedure and high atom economy. Further, the methodology developed by us can also be used to generate symmetrical alpha,alpha-disubstituted aldehydes through an alternative decomposition method.

摘要

通过卤代烷烃的烷基化反应，对亲核β-丙氨酸等价物β-Ala Ni(II)-PABP [β-丙氨酸席夫碱与 2-[N-(α-吡啶基)氨基]二苯甲酮（PABP）的 Ni(II)配合物，1]的同系化进行了系统研究，这是一种合成对称的α,α-二取代β-氨基酸的通用方法。二烷基化反应易于进行，且不需要惰性气氛、干燥溶剂和低温，因此具有操作方便的实验程序和高原子经济性的优点。此外，我们开发的方法也可以通过替代的分解方法生成对称的α,α-二取代醛。

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