Correspondence concerning single-crystal X-ray analyses should be directed to this author).
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Full Paper
New Proline–Oxazoline Ligands and Their Application in the Asymmetric Nozaki–Hiyama–Kishi Reaction
Article first published online: 18 JUN 2007
DOI: 10.1002/ejoc.200700227
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Hargaden, G. C., Müller-Bunz, H. and Guiry, P. J. (2007), New Proline–Oxazoline Ligands and Their Application in the Asymmetric Nozaki–Hiyama–Kishi Reaction. Eur. J. Org. Chem., 2007: 4235–4243. doi: 10.1002/ejoc.200700227
Publication History
- Issue published online: 10 AUG 2007
- Article first published online: 18 JUN 2007
- Manuscript Received: 14 MAR 2007
Funded by
- Centre for Synthesis and Chemical Biology
- Abstract
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- Cited By
Keywords:
- Asymmetric catalysis;
- Oxazolines;
- Proline;
- Ligands;
- Allylation
Abstract
Sixteen members of a new ligand class incorporating an oxazoline ring linked by an amide bond to a chiral protected proline unit were prepared in a high-yielding four-step synthesis from readily available chiral amino alcohols and N-protected proline. The ligands were applied in the enantioselective Nozaki–Hiyama–Kishi allylation of benzaldehyde and gave enantioselectivities of up to 57 %. Diastereomeric ligand pairs were prepared to determine the role of each chiral centre in enantioselection.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)