Modular synthesis of allyl vinyl ethers for the enantioselective construction of functionalized quaternary stereocenters

Abstract

A concise synthesis of 2-t-butoxycarbonyl allyl vinyl ethers by regioselective Petasis methylenation and stereoselective Suzuki–Miyaura cross-coupling reactions of iodoallyl t-butyl oxalates was developed. Ethers with a terminally unsubstituted vinyl group and a terminally disubstituted allyl portion are readily accessible by this method. The enantioselective Claisen rearrangement of representative allyl vinyl ethers was examined.