Efficient one-step synthesis of chiral bidentate oxazoline-alcohol ligands via a cyclic imidate ester rearrangement

…, K Robeyns, L Van Meervelt, E Van der Eycken…

Index: Noel, Timothy; Robeyns, Koen; Meervelt, Luc Van; Eycken, Erik Van der; Eycken, Johan Van der Tetrahedron Asymmetry, 2009 , vol. 20, # 17 p. 1962 - 1968

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Citation Number: 15

Abstract

Various chiral bidentate oxazoline-alcohol ligands were obtained in a straightforward one- step synthesis via a cyclic imidate ester rearrangement. These chiral ligands were tested and compared in asymmetric diethylzinc additions to aldehydes resulting in selectivities of up to 87% ee. An interesting chirality switch was observed when a CPh2-tether instead of a CH2 was present, offering the opportunity for dual stereocontrol.