Synthesis of Spiro Ketals, Orthoesters, and Orthocarbonates by CpRu-Catalyzed Decomposition of α-Diazo-β-ketoesters

Cecilia Tortoreto; Thierry Achard; Léo Egger; Laure Guénée; Jérôme Lacour

doi:10.1021/acs.orglett.5b03380

Synthesis of Spiro Ketals, Orthoesters, and Orthocarbonates by CpRu-Catalyzed Decomposition of α-Diazo-β-ketoesters

Org Lett. 2016 Jan 15;18(2):240-3. doi: 10.1021/acs.orglett.5b03380. Epub 2015 Dec 28.

Authors

Cecilia Tortoreto¹, Thierry Achard¹, Léo Egger¹, Laure Guénée², Jérôme Lacour¹

Affiliations

¹ Department of Organic Chemistry, University of Geneva , Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
² Laboratory of Crystallography, University of Geneva , Quai Ernest Ansermet 24, CH-1211 Geneva 4, Switzerland.

PMID: 26709440
DOI: 10.1021/acs.orglett.5b03380

Abstract

Reactions of α-diazo-β-ketoesters with cyclic ketones, lactones, and carbonates are reported. Thanks to the combined use of salt [CpRu(CH3CN)3][BArF] and 1,10-phenanthroline as catalyst for the diazo decomposition, effective and practical syntheses of spiro bicyclic ketals, orthoesters, and orthocarbonates are afforded.

Publication types

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