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Rae J, Hu YC, Procter DJ. Cu(I)-NHC-catalyzed silylation of allenes: diastereoselective three-component coupling with aldehydes. Chemistry. 2014;20(41):13143-5doi: 10.1002/chem.201404330.
Rae, J., Hu, Y. C., & Procter, D. J. (2014). Cu(I)-NHC-catalyzed silylation of allenes: diastereoselective three-component coupling with aldehydes. Chemistry (Weinheim an der Bergstrasse, Germany), 20(41), 13143-5. https://doi.org/10.1002/chem.201404330
Rae, James, et al. "Cu(I)-NHC-catalyzed silylation of allenes: diastereoselective three-component coupling with aldehydes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,41 (2014): 13143-5. doi: https://doi.org/10.1002/chem.201404330
Rae J, Hu YC, Procter DJ. Cu(I)-NHC-catalyzed silylation of allenes: diastereoselective three-component coupling with aldehydes. Chemistry. 2014 Oct 06;20(41):13143-5. doi: 10.1002/chem.201404330. Epub 2014 Aug 21. PMID: 25146221.
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Chemistry. 2014 Oct 06;20(41):13143-5. doi: 10.1002/chem.201404330. Epub 2014 Aug 21.

Cu(I)-NHC-catalyzed silylation of allenes: diastereoselective three-component coupling with aldehydes.

Chemistry (Weinheim an der Bergstrasse, Germany)

James Rae, Ya Chu Hu, David J Procter

Affiliations

  1. School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL (UK) http://people.man.ac.uk/?mbdssdp2/

PMID: 25146221 DOI: 10.1002/chem.201404330

Abstract

Copper-catalyzed silylation of aryl allenes using a silylborane reagent affords vinyl silane building blocks with high efficiency. The use of a seven-membered NHC ligand proved crucial for high regioselectivity. The catalytically generated allylcoppper intermediates were intercepted by aldehydes in a diastereoselective three-component coupling to furnish homoallylic alcohols.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: N-heterocyclic carbenes; allenes; copper; homogeneous catalysis; silylation

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