Njiojob Costyl N, Rhinehart Jennifer L, Bozell Joseph J, Long Brian K
Department of Chemistry, University of Tennessee , Knoxville, Tennessee 37996, United States.
J Org Chem. 2015 Feb 6;80(3):1771-80. doi: 10.1021/jo502685k. Epub 2015 Jan 27.
A series of highly enantioselective transformations, such as the Sharpless asymmetric epoxidation and Jacobsen hydrolytic kinetic resolution, were utilized to achieve the complete stereoselective synthesis of β-O-4 lignin dimer models containing the S, G, and H subunits with excellent ee (>99%) and moderate to high yields. This unprecedented synthetic method can be exploited for enzymatic, microbial, and chemical investigations into lignin's degradation and depolymerization as related to its stereochemical constitution. Preliminary degradation studies using enantiopure Co(salen) catalysts are also reported.
利用了一系列高度对映选择性转化反应，如夏普莱斯不对称环氧化反应和雅各布森水解动力学拆分反应，以实现完全立体选择性合成含有S、G和H亚基的β-O-4木质素二聚体模型，其对映体过量值（ee）优异（>99%），产率适中至高。这种前所未有的合成方法可用于对木质素与其立体化学结构相关的降解和解聚进行酶学、微生物学和化学研究。还报道了使用对映体纯的Co（salen）催化剂进行的初步降解研究。
