(Chemical Equation Presented) A direct catalytic asymmetric aldol reaction of thioamides with a soft Lewis acid/hard Brønsted base cooperative catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]PF6/LiOAr is described. Highly chemoselective deprotonative activation of thioamides allows for a direct aldol reaction of α-nonbranched aliphatic aldehydes, which are susceptible to self-condensation. Facile reduction of the thioamide functionality and a catalyst-controlled second aldol reaction provides 1,3-diols in a highly stereoselective manner.
All Science Journal Classification (ASJC) codes
- General Chemistry
- Colloid and Surface Chemistry