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Synthesis 2010(19): 3243-3247  
DOI: 10.1055/s-0030-1258203
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Exploring Rhodium-Catalysed Conjugate Addition of Chiral Alkenylboronates Using Chiral Olefin Ligands

Christopher G. Frost*a, Hannah J. Edwardsa, Stephen D. Penrosea, Robert Gleaveb
a Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK
Fax: +44(1225)386231; e-Mail: c.g.frost@bath.ac.uk;
b Neurology and Gastrointestinal Centre of Excellence for Drug Discovery, GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK
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Publikationsverlauf

Received 4 May 2010
Publikationsdatum:
13. August 2010 (online)

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Abstract

The rhodium-catalysed addition of chiral alkenylboron reagents to prochiral α,β-unsaturated carbonyl acceptors are demonstrated to proceed under ligand control. The highest activities were obtained with chiral olefin ligands and the configuration of the new stereocentre can be predicted by using established models.

Key words

alkenylboronate - conjugate addition - rhodium - catalysis - chiral olefin ligands

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