Collect. Czech. Chem. Commun. 2011, 76, 415-422
https://doi.org/10.1135/cccc2011024
Published online 2011-04-07 21:46:10

Enantioselective epoxide ring opening catalyzed by bis(tetrahydroisoquinoline) N,N′-dioxides

Aneta Kadlčíkováa, Klára Vlašanáa and Martin Kotoraa,b,*

a Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Prague 2, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

Abstract

Four bis(tetrahydroisoquinoline) N,N′-dioxides were used as catalysts for the epoxide ring opening with tetrachlorosilane under various conditions. A strong solvent effect on asymmetric induction was observed for each of the used catalysts. The highest achieved asymmetric induction for the opening of meso-stilbene oxide was 69% ee. Regarding the cycloalkene oxides, 56% ee was obtained in the reaction with cyclooctene oxide.

Keywords: Asymmetric catalysis; Silanes; N ligands; Enantioselectivity.

References: 25 live references.

This article is part of virtual issue Prof. Pavel Kočovský, FRSE
60th Birthday.