Synthesis of a chiral phosphonium salt for the preparation of α-substituted alaninol derivatives

Abstract

We herein report the synthesis of a chiral phosphonium salt, {[(4S)-4-methyl-2-oxo-1,3-oxazolidin-4-yl]methyl}(triphenyl)phosphonium iodide 13 to provide a new Wittig reagent for the general method of synthesizing α-substituted alaninol derivatives. Our method described here is widely applicable to reactions with various types of aldehyde to afford olefin products with high E-selectivity, enabling us to provide a new approach to the synthesis of chiral S1P1 agonists including our key intermediates, and of the trace amine-associated receptor 1 (TAAR1) agonist.