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

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

Chem Commun (Camb). 2012 Nov 18;48(89):11029-31. doi: 10.1039/c2cc36656h.

Authors

Marta Woyciechowska¹, Gwenael Forcher, Szymon Buda, Jacek Mlynarski

Affiliation

¹ Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland.

PMID: 23037879
DOI: 10.1039/c2cc36656h

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Catalysis
Furans / chemistry*
Lewis Acids / chemistry
Molecular Structure
Siloxanes / chemistry*
Stereoisomerism
Water / chemistry*

Substances

Aldehydes
Furans
Lewis Acids
Siloxanes
Water
3-hydroxybutanal