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Practical Asymmetric Synthesis of Trifluoromethyl-Containing Aminoester Using a Modified Davis Protocol

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journal contribution
posted 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.