Journal
ORGANIC LETTERS
Volume 20, Issue 3, Pages 554-557Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03637
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Funding
- National Basic Research Program [2015CB856600]
- National Natural Science Foundation of China [21502020]
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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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