Benzoic acid, 4-methoxy-, (1Z)-1-hexenyl ester

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CAS: 555154-54-6
MF: C14H18O3
MW: 234.29092
Synonyms: Benzoic acid, 4-methoxy-, (1Z)-1-hexenyl ester

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Steven Feldgus Steven

University of Wisconsin-Madison
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Gregory K. Friestad

University of Iowa
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Co-reporter: Gregory K. Friestad, Gopeekrishnan Sreenilayam, Joseph C. Cannistra, Luke M. Slominski
pp: 5064-5067
Publication Date(Web):19 September 2012
DOI: 10.1016/j.tetlet.2012.06.142
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.Image for unlabelled figure