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

Authors :
KU LEUVEN - Department of Chemistry
Noël, Timothy
Robeyns, Koen
Van Meervelt, Luc
Van der Eycken, Erik
Van der Eycken, Johan
KU LEUVEN - Department of Chemistry
Noël, Timothy
Robeyns, Koen
Van Meervelt, Luc
Van der Eycken, Erik
Van der Eycken, Johan
Source :
Tetrahedron Asymmetry, Vol. 20, no. 17, p. 1962-1968 (2009)
Publication Year :
2009

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. © 2009 Elsevier Ltd. All rights reserved.

Details

Database :
OAIster
Journal :
Tetrahedron Asymmetry, Vol. 20, no. 17, p. 1962-1968 (2009)
Notes :
0en
Publication Type :
Electronic Resource
Accession number :
edsoai.on1104535928
Document Type :
Electronic Resource