Isocyanides are a unique class of functional group that rapidly assemble heterocycles and peptidomimetics. Building on our recent anionic route to functionalized disubstituted and trisubstituted isocyanides with Asmic (Anisylsulfanylmethylisocyanide), we have discovered a remarkable dearomatization that occurs within 15 minutes at -78 oC to afford complex cyclohexadienes. The cyclohexadiene incorporates two equivalents of disubstituted Asmic with formation of two all carbon quaternary stereocenters and three orthogonal functionalities: an enol ether, an isocyanide and a nitrile. The three functional groups provide different sites ideally suited for selective synthetic elaboration. The reaction scope, a mechanistic analysis, reactions that elaborate the cyclohexadiene scaffold will be presented.

Rapid isocyanide-induced dearomatization to complex cyclohexadienes

Macromolecular Chemistry: The Second Century

[Author Benefits](https://scimeetings.acs.org/?utm_source=pubs_content_marketing&utm_medium=website&utm_campaign=0320_MCF_NPI_Launch_Spring_Homepage&ref=pubs_content_marketing)

[How to use SciMeetings](https://storage.googleapis.com/dl.morressier.com/acs/SciMeetings-ACSSpring2020-HowToGuide_M3020-Final.pdf)

[Frequently Asked Questions](https://storage.googleapis.com/dl.morressier.com/acs/SciMtng_ACSNMSp2020_FAQ_M3120_Final.pdf)

ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.