Practical Asymmetric Synthesis of Trifluoromethyl-Containing Aminoester Using a Modified Davis Protocol
journal contributionposted on 16.05.2008, 00:00 by Asaf Alimardanov, Jean Schmid, Jay Afragola, Gulnaz Khafizova
Practical synthesis of aminoester 1 starting from 1,1,1-trifluoro-3-iodopropane is presented. Use of Ti(Oi-Pr)4 as a Lewis acid for condensation of intermediate aldehyde 8 with (S)-(+)-p-toluenesulfinamide was found to be critical. Conditions for a reproducible and high-yielding Wittig reaction of aldehyde hydrate with phosphorus ylide 4, that appear to have general applicability, are described.