Asymmetric Intramolecular Cyclobutane Formation via Photochemical Reaction of N,N-Diallyl-2-quinolone-3-carboxamide Using a Chiral Crystalline Environment

Crystal structures and photochemical reactions of three N,N-diallyl-2-quinolone-3-carboxamides were investigated. One quinolonecarboxamide afforded chiral crystals of a P21 crystal system by spontaneous crystallization, and the molecular chirality in the crystal was effectively transferred to cyclobutane in 96% ee by an intramolecular 2 + 2 photocycloaddition reaction in the solid state.

本研究对三种N,N-二烯丙基-2-喹啉酮-3-甲酰胺（N,N-diallyl-2-quinolone-3-carboxamides）的晶体结构与光化学反应进行了系统探究。其中一种喹啉酮甲酰胺经自发结晶过程，得到了属于P21晶系的手性晶体；在固态条件下，通过分子内2+2光环加成反应，该晶体中的分子手性可高效传递至环丁烷产物，对映选择性达96% ee。