The Synthesis of 4??Hydroxypipecolic Acids by Stereoselective Cycloaddition of Configurationally Stable Nitrones

FM Cordero, S Bonollo, F Machetti…

Index: Cordero, Franca M.; Bonollo, Simona; Machetti, Fabrizio; Brandi, Alberto European Journal of Organic Chemistry, 2006 , # 14 p. 3235 - 3241

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Citation Number: 11

Abstract

Abstract The diastereoselective synthesis of trans-and cis-4-hydroxypipecolic acids has been achieved with geometry-controlled nitrone cycloaddition chemistry. The cycloaddition of 3-butenol to enantiopure C-aminocarbonyl and C-alkoxycarbonyl nitrones having a definite (Z) and (E) configuration, respectively, occurs with complete regio-and exo selectivity. The acyclic (Z)-nitrone 12 affords two cycloadducts in a 1: 1 ratio, which can be ...

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