Cross-Coupling of Organoindium Reagents with Propargylic Esters

Significance

The chemistry of organoindium compounds is becoming a useful tool in modern organic synthesis. The method presented herein allows a simple preparation of various allenes, including chiral ones, starting from readily available propargylic esters. Organoindium compounds tolerate a variety of functional groups, therefore the method can be useful for the preparation of functionalized allenes. Aryl, alkenyl and alkynyl indium derivatives are suitable reagents. The process is highly anti-stereoselective, and a good degree of chirality transfer was observed for enantiopure substrates. The reaction proceeds smoothly at room temperature.