Intramolecular Propargylic Ene Reaction of Benzyne En Route to Highly Functionalized Allenes and Allenamides

A variety of highly functionalized allenes and allenamides are prepared by intramolecular propargylic ene reactions of benzynes. Specific benzyne precursors having a chlorodiisopropylsilyl group serve as platforms to link with various propargyl alcohols via a Si-O bond, thereby expanding the scope of this reaction. Also demonstrated is a complete transmission of point to axial chirality to give a chiral, nonracemic allenamide.

Automated summary

A variety of highly functionalized allenes and allenamides are prepared by intramolecular propargylic ene reactions of benzynes. Specific benzyne precursors are used as a platform to link with various propargyl alcohols via a Si-O bond, expanding the scope of this reaction. Additionally, a complete transmission of point to axial chirality is demonstrated, resulting in a chiral, nonracemic allenamide.