Aldol reaction of 3,3,3-trifluoropropionates

Pravin D Gagare, Purdue University

Abstract

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. ^

Degree

Ph.D.

Advisors

P. V. Ramachandran, Purdue University.

Subject Area

Chemistry, Organic

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