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Matched Coupling of Propargylic Carbonates with Cyclopropanols
Penglin Wu1, Minqiang Jia1, Weilong Lin2
1Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University , 220 Handan Road, Shanghai 200433, P. R. China.
Abstract:
The ring opening-coupling reaction of cyclopropanols with propargylic carbonates affording synthetically attractive allenyl ketones has been developed. The mechanism involves the ligand-exchange reaction of in situ formed allenyl palladium methoxide with cyclopropanols followed by carbon-carbon bond cleavage and reductive elimination. The reactions proceeded smoothly under mild reaction conditions with Pd(0)/XPhos catalysis in the absence of any external base and displayed a wide scope and application to a steroidal skeleton. The efficiency of chirality transfer and synthetic utility of the allene products have also been demonstrated.
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