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Sweets for Catalysis – Facile Optimisation of Carbohydrate-Based Bis(oxazoline) Ligands

✍ Scribed by Tobias Minuth; Mustafa Irmak; Annika Groschner; Tobias Lehnert; Mike M. K. Boysen

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
483 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A new type of carbohydrate‐based bis(oxazoline) ligands was prepared from inexpensive D‐glucosamine and tested in asymmetric cyclopropanation reactions. For optimisation, modified ligands with 3‐O substituents of varying size and electronic properties were prepared as well as a 3‐OH unprotected and a perpivaloylated derivative. All new ligands were tested in asymmetric cyclopropanation, revealing a strong dependence of enantioselectivity on steric demand and electronic properties of the 3‐O residue. Also, a significant influence of the pyranose conformation, which is determined by the presence or absence of the cyclic acetal group, was observed. Thus, it was easily possible to tune the new carbohydrate bis(oxazoline) ligands to a given reaction.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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