甘氨酸席夫碱的NH型手性镍（II）配合物：设计、结构评估、反应性及合成应用

NH-type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications.

作者信息

Bergagnini Mackenzie, Fukushi Kazunobu, Han Jianlin, Shibata Norio, Roussel Christian, Ellis Trevor K, Aceña José Luis, Soloshonok Vadim A

机构信息

Department of Chemistry and Physics, Southwestern Oklahoma State University, 100 Campus Drive, Weatherford, OK 73096-3098, USA.

出版信息

Org Biomol Chem. 2014 Feb 28;12(8):1278-91. doi: 10.1039/c3ob41959b.

DOI:10.1039/c3ob41959b

PMID:24424805

Abstract

The work being reported here deals with the design of a new type of "N-H" Ni(II) complexes of glycine Schiff bases and study general aspects of their reactivity. It was confirmed that the presence of NH function in these Ni(II) complexes does not interfere with the homologation of the glycine residue, rendering these derivatives of high synthetic value for the general synthesis of α-amino acids. In particular, the practical application of these NH-type complexes was demonstrated by asymmetric synthesis of various β-substituted pyroglutamic acids via Michael addition reactions with chiral Michael acceptors.

摘要

本文所报道的工作涉及甘氨酸席夫碱新型“N-H”镍（II）配合物的设计，并研究其反应的一般方面。已证实这些镍（II）配合物中NH官能团的存在不干扰甘氨酸残基的同系化，使得这些衍生物对于α-氨基酸的一般合成具有很高的合成价值。特别地，通过与手性迈克尔受体的迈克尔加成反应不对称合成各种β-取代焦谷氨酸，证明了这些NH型配合物的实际应用。