Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prepare α-aryl- and α-alkyl seleno methylketones through a single chemical operation. No racemization events are observed in the presence of optically pure starting materials.

Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry [Expeditious and Chemoselective Synthesis of alpha-Aryl and alpha-Alkyl Selenomethylketones via Homologation Chemistry] / R. Senatore, L. Castoldi, L. Ielo, W. Holzer, V. Pace. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 20:9(2018 May 04), pp. 2685-2688. [10.1021/acs.orglett.8b00896]

Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry [Expeditious and Chemoselective Synthesis of alpha-Aryl and alpha-Alkyl Selenomethylketones via Homologation Chemistry]

L. Castoldi
Secondo
;
2018

Abstract

Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prepare α-aryl- and α-alkyl seleno methylketones through a single chemical operation. No racemization events are observed in the presence of optically pure starting materials.
Settore CHIM/06 - Chimica Organica
17-apr-2018
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890731
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