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 ...
[Rutjes, Floris P. J. T.; Veerman, Johan J. N.; Meester, Wim J. N.; Hiemstra, Henk; Schoemaker, Hans E. European Journal of Organic Chemistry, 1999 , # 5 p. 1127 - 1135]
