Aldol reaction of 3,3,3-trifluoropropionates
Reported herein is the diastereoselective and enantioselective aldol reaction of 3,3,3-trifluoropropionates. The initial study of enolboration-aldolization of these esters with di-n-butylboron triflate, and dicyclohexylboron triflate is discussed. The development of bis-exo-2-norbornylboron triflate as a reagent for the facile, diastereospecific incorporation of anti-α-trifluoromethyl β-hydroxy moieties is also discussed. The first application of dialkylchloroborane for diastereospecific enolization of 3,3,3-trifuoropropionates has been described. The systematic examination of double diastereoselective aldol reaction of 3,3,3-trifluoropropionates with (+)/(-)-diisopinocampheylboron triflate and (+)/(-)-diisopinocampheylboron chloride is discussed. The development of 2-(arylmethoxy)isopinocampheols as novel chiral auxiliaries and its application for double diastereoselective aldol reaction is also discussed. ^
P. V. Ramachandran, Purdue University.