Jump to Main Content
Chemoselective Intramolecular Carbonyl Ylide Formation through Electronically Differentiated Malonate Diesters
- Nakhla, Mina C., Lee, Che-Wah, Wood, John L.
- Organic letters 2015 v.17 no.23 pp. 5760-5763
- alkynes, catalysts, catalytic activity, chemical reactions, chemical structure, chemoselectivity, diastereoselectivity, diazo compounds
- 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.