Preparation of enol ester epoxides and their ring-opening to α-silyloxyaldehydes

Gregory K Friestad; Gopeekrishnan Sreenilayam; Joseph C Cannistra; Luke M Slominski

doi:10.1016/j.tetlet.2012.06.142

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Preparation of enol ester epoxides and their ring-opening to α-silyloxyaldehydes

Journal article

Peer reviewed

Preparation of enol ester epoxides and their ring-opening to α-silyloxyaldehydes

Gregory K Friestad, Gopeekrishnan Sreenilayam, Joseph C Cannistra and Luke M Slominski

Tetrahedron letters, Vol.53(38), pp.5064-5067

09/19/2012

DOI: 10.1016/j.tetlet.2012.06.142

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Abstract

The Z-selective ruthenium-catalyzed addition of aromatic carboxylic acids to alkynes was followed by dioxirane epoxidation to furnish enol ester epoxides with cis configuration. Upon treatment of enol ester epoxides with tert-butyldimethylsilyl triflate in the presence of 2,6-lutidine, synthetically useful α-silyloxyaldehydes were obtained. This novel transformation was facilitated by microwave irradiation.

Oxidation

Enol esters

Epoxides

Aldehydes

Details

Title: Subtitle: Preparation of enol ester epoxides and their ring-opening to α-silyloxyaldehydes
Creators: Gregory K Friestad
Gopeekrishnan Sreenilayam
Joseph C Cannistra
Luke M Slominski
Resource Type: Journal article
Publication Details: Tetrahedron letters, Vol.53(38), pp.5064-5067
Publisher: Elsevier Ltd
DOI: 10.1016/j.tetlet.2012.06.142
ISSN: 0040-4039
eISSN: 1873-3581
Language: English
Date published: 09/19/2012
Academic Unit: Chemistry
Record Identifier: 9983985877402771

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