Terpenoid Cyclophanes\nwith Planar Chirality

The strain-induced chirality of cyclophanes has attracted\ninterest\nwithin the synthetic community. Herein, we report the synthesis of\nanilinocyclophanes derived from naturally occurring terpenes, such\nas citronellol, geraniol, and farnesol. The resulting cyclic oligoprenyl\nmolecules exhibit considerable ring strain (up to 31 kcal/mol), as\nevident from their bent aniline planes, and possess chirality across\nthe planes of an aryl ring and double bonds. Unexpected outcomes,\nsuch as the formation of isomerized neraniline, highlight the influence\nof ring strain on the stability and reactivity of terpenoid <i>para</i>-cyclophanes.