The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes

Lei Zhang; Christine M Le; Mark Lautens

doi:10.1002/anie.201400218

The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes

Angew Chem Int Ed Engl. 2014 Jun 2;53(23):5951-4. doi: 10.1002/anie.201400218. Epub 2014 Apr 25.

Authors

Lei Zhang¹, Christine M Le, Mark Lautens

Affiliation

¹ Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada).

PMID: 24771670
DOI: 10.1002/anie.201400218

Abstract

Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium-catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene natural products.

Keywords: asymmetric catalysis; rhodium; silyl ketene acetals; strained molecules.

Publication types

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

MeSH terms

Acetals / chemistry*
Alkenes / chemistry*
Catalysis
Ethers / chemistry*
Ethylenes / chemistry*
Ketones / chemistry*
Stereoisomerism

Substances

Acetals
Alkenes
Ethers
Ethylenes
Ketones
ketene