Enantiospecific Generation and Trapping Reactions of Aryne Atropisomers

Enantioenriched aryne
atropisomers having a biaryl stereogenic
axis vicinal to the reactive triple bond are demonstrated to exist.
These reaction intermediates are easily produced in situ and can undergo
the standard aryne cycloaddition chemistry in an enantiospecific manner.
Notably, the aryne atropisomers herein have allowed the practical
syntheses of a small nanographene as well as some triptycene and anthracene
derivatives that embed stereogenic axes of controlled absolute configurations.

研究证实，存在一类对映富集的芳炔(aryne)阻转异构体，其联芳基手性轴紧邻反应性三键。这类反应中间体可便捷地原位生成，并能以对映专一性的方式参与经典的芳炔环加成反应。值得注意的是，本文所研究的芳炔阻转异构体可用于高效合成一类小型纳米石墨烯，以及若干带有可控绝对构型手性轴的三蝶烯(triptycene)和蒽(anthracene)衍生物。