Highly Regio‐ and Stereoselective Synthesis of Nine‐ to Twelve‐Membered Cyclic Compounds by a Pd0‐Catalyzed Cyclization Reaction between Allenes with a Nucleophilic Functionality and Organic Halides

Abstract

Simple cyclization: A novel method has been developed for the highly regio- and stereoselective synthesis of nine- to twelve-membered cyclic compounds by a Pd0-catalyzed cyclization reaction of allenes with a carbon or nitrogen nucleophilic functionality. Oxidative addition and carbopalladation gave anti-π-allyl palladium intermediates, then an exclusive intramolecular nucleophilic attack at the terminal carbon atom of the allene moiety gave the E product in good yields (see scheme; Ts=tosyl; DMA=N,N-dimethylacetamide).