American Chemical Society
ol5b02847_si_002.cif (1.11 MB)

Chemoselective Intramolecular Carbonyl Ylide Formation through Electronically Differentiated Malonate Diesters

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posted on 2015-12-04, 00:00 authored by Mina C. Nakhla, Che-Wah Lee, John L. Wood
A method for chemoselective carbonyl ylide formation utilizing the Rh­(II) catalyzed decomposition of electronically differentiated diazo malonates is disclosed. Treatment of ethyl, trifluoro ethyl diazo malonate with a Rh­(II) catalyst selectively forms a carbonyl ylide from the relatively electron rich ethyl ester. This carbonyl ylide can be trapped by various alkynes giving highly functionalized oxabicyclic compounds in a chemo-, regio-, and diastereoselective fashion.