General switch in regioselectivity in the Mukaiyama aldol reaction of silyloxyfuran with aldehydes in aqueous solvents

Marta Woyciechowska; Gwenael Forcher; Szymon Buda; Jacek Mlynarski

doi:10.1039/C2CC36656H

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Chemical Communications

Issue 89, 2012

Urgent high quality communications from across the chemical sciences.

Impact Factor 6.169 100 Issues per Year Indexed in MEDLINE

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General switch in regioselectivity in the Mukaiyama aldol reaction of silyloxyfuran with aldehydes in aqueous solvents

Marta Woyciechowska,^a Gwenael Forcher,^a Szymon Buda^a and Jacek Mlynarski*^a^b

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Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
E-mail: jacek.mlynarski@gmail.com

Chem. Commun., 2012,48, 11029-11031

DOI: 10.1039/C2CC36656H
Received 30 Jul 2012, Accepted 20 Sep 2012
First published online 26 Sep 2012

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Abstract
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An unexpected yet disciplined course of catalytic Mukaiyama-aldol reaction instead of the expected vinylogous Mukaiyama-aldol reaction has been observed for the reaction of silyloxyfuran with various aldehydes under Lewis acid catalytic control in water-containing solvents.

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General switch in regioselectivity in the Mukaiyama aldol reaction of silyloxyfuran with aldehydes in aqueous solvents

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