Cookies on this website

We use cookies to ensure that we give you the best experience on our website. If you click 'Accept all cookies' we'll assume that you are happy to receive all cookies and you won't see this message again. If you click 'Reject all non-essential cookies' only necessary cookies providing core functionality such as security, network management, and accessibility will be enabled. Click 'Find out more' for information on how to change your cookie settings.

Members of a family of functionally and stereochemically diverse d-glucosamine-derived tertiary aminoalcohol ligands have been used to promote the asymmetric Reformatsky reaction. The β-hydroxyester product tert-butyl 3-phenyl-3-hydroxy-propanoate was obtained enriched in either the (+)-(R) (up to 74% ee) or (-)-(S) (up to 42% ee) enantiomer depending on the choice of ligand. Although the selectivities are modest in absolute terms they represent some the better selectivities obtained to date for this reaction. A 1H NMR study was conducted to investigate this selectivity and suggested a secondary binding mode between ligand and zinc in addition to the expected N-2, O-3 coordination. © 2004 Elsevier Ltd. All rights reserved.

Original publication




Journal article


Tetrahedron Asymmetry

Publication Date





213 - 221