Asymmetric total synthesis of (+)-indatraline via diastereoselective amination of chiral ethers using chlorosulfonyl isocyanate

Abstract

A concise asymmetric total synthesis of (+)-indatraline from readily available cinnamic acid is described. The key steps include Corey's oxazaborolidine-catalyzed asymmetric carbonyl reduction and a highly stereoselective amination of chiral benzylic ether with retention of stereochemistry using chlorosulfonyl isocyanate.