Boron-mediated aldol reaction of carboxylic esters: complementary anti-and syn-selective asymmetric aldol reactions

T Inoue, JF Liu, DC Buske, A Abiko

Index: Inoue, Tadashi; Liu, Ji-Feng; Buske, Dana C.; Abiko, Atsushi Journal of Organic Chemistry, 2002 , vol. 67, # 15 p. 5250 - 5256

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Citation Number: 91

Abstract

The boron-mediated aldol reaction of carboxylic esters is described in detail. Contrary to the general belief that carboxylic esters are inert under the condition of the boron enolate formation, propionate esters are enolized with certain combinations of a boron triflate and an amine. More importantly, the stereochemical course of the aldol reaction can be controlled by the judicious selection of the enolization reagents. Treatment of propionate esters with ...