The catalytic decarboxylative allylation of enol carbonates: the synthesis of enantioenriched 3-allyl-3'-aryl 2-oxindoles and the core structure of azonazine.

Abstract

The catalytic asymmetric synthesis of 3-allyl-3'-aryl 2-oxindoles has been shown via the Pd(0)-catalyzed decarboxylative allylation of allylenol carbonates. This methodology provides access to a variety of 2-oxindole substrates (5a-v) with all-carbon quaternary stereocenters (up to 94% ee) at the pseudobenzylic position under additive-free and mild conditions. The synthetic potential of this method was shown by the asymmetric synthesis of the tetracyclic core of the diketopiparazine-based alkaloid azonazine (11).