Bridged‐Ring Skeletons from Organoaluminium‐Mediated Nucleophilic Addition‐Cyclization Sequence of p‐Quinone Monoacetals and Grignard Reagents

Abstract

AbstractDescribed herein is the development of an organoaluminium‐mediated tandem conjugate addition‐cyclization sequence of p‐quinone monoacetals with 2‐siloxyphenyl Grignard reagents to afford a collection of phenol‐bridged cyclohexanone derivatives. Furthermore, a tandem conjugate‐addition and dimerization reaction of p‐quinone monoacetals with Grignard reagents is also reported to offer a straightforward and diastereoselective synthesis of complex bridged‐ring compounds bearing tricyclo[6.2.2.02,7]dodecene skeletons.