Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NCOOH

Abstract: The SN2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N–R′COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR′COOH is crucial for the SN2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3–13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14–24 (Scheme 2) in good to high yields. [Copyright &y& Elsevier]