A non-diazo strategy to cyclopropanation via oxidatively generated gold carbene: The benefit of a conformationally rigid P,N-bidentate ligand?
Organic Chemistry Frontiers Pub Date: 2014-02-13 DOI: 10.1039/C3QO00080J
Abstract
What a trade: diazo ketones for alkynes? By utilizing a conformationally rigid P,N-bidentate ligand, highly efficient intramolecular cyclopropanation reactions using flexible and electronically neutral terminal alkyne substrates are realized via a sterically shielded tri-coordinated gold carbene intermediate. Bicyclic/tricyclic functionalized cyclopropyl ketones are formed in mostly good yields in three steps from readily available enones/enals, which compares favorably with related strategies based on the diazo approach in terms of step economy and operational safety. With this chemistry, we have expanded alkynes as surrogates of α-diazo ketones to cyclopropanation reactions.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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