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Modular synthesis of allyl vinyl ethers for the enantioselective construction of functionalized quaternary stereocenters†
Gopinathan Muthusamy,Sunil V. Pansare
RSC Advances Pub Date : 10/27/2016 00:00:00 , DOI:10.1039/C6RA24284G
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.

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