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Issue 25, 2017
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Enantioselective Barbier-type allylation of ketones using allyl halide and indium in water

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Abstract

We disclose herein an efficient enantioselective Barbier-type allylation of ketones using allyl halide and indium metal in water. The reaction was catalysed by chiral bis(imidazoline) to afford homoallylic alcohols having quaternary stereocenters in good yield with moderate to good enantioselectivity. Based on experimental investigation, a possible transition state has been proposed to explain the origin of the asymmetric induction.

Graphical abstract: Enantioselective Barbier-type allylation of ketones using allyl halide and indium in water

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Supplementary files

Article information


Submitted
23 Jan 2017
Accepted
03 Mar 2017
First published
09 Mar 2017

This article is Open Access

RSC Adv., 2017,7, 15582-15585
Article type
Paper

Enantioselective Barbier-type allylation of ketones using allyl halide and indium in water

S. Nakamura, Y. Hara, T. Furukawa and T. Hirashita, RSC Adv., 2017, 7, 15582
DOI: 10.1039/C7RA01038A

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