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

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.

Automated summary

This paper describes the development of a tandem conjugate addition-cyclization sequence of p-quinone monoacetals with 2-siloxyphenyl Grignard reagents, resulting in the synthesis of phenol-bridged cyclohexanone derivatives. It also reports a tandem conjugate-addition and dimerization reaction of p-quinone monoacetals with Grignard reagents, leading to the diastereoselective synthesis of complex bridged-ring compounds bearing tricyclo[6.2.2.0(2,7)]dodecene skeletons.