Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, S3 7HF, UK.
Org Biomol Chem. 2011 Jun 7;9(11):4353-60. doi: 10.1039/c1ob05129f. Epub 2011 Apr 20.
Highly stereoselective Friedel-Crafts reactions have been performed using a chiral anthracene template to control the selectivity of the reaction. In the case of additions to fully substituted N-acyliminium ions, competitive elimination and condensation reactions were observed. Retro-Diels-Alder reaction of one of the reaction products led to a precursor that could be used for the construction of pyroglutamic acids bearing quaternary stereogenic centres.
使用手性蒽模板进行高立体选择性傅克反应,以控制反应的选择性。在完全取代的 N-酰亚胺离子加成的情况下,观察到竞争性消除和缩合反应。其中一个反应产物的逆狄尔斯-阿尔德反应生成了一个前体,可用于构建带有季立体中心的吡咯烷酮酸。