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

Abstract Described 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[6.2.2.0 2,7 ]dodecene skeletons.