Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 6805-6810Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02431
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Funding
- National Natural Science Foundation of China (NSFC) [21772215, 21532010, 21472214]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20030100]
- NSFC [21361162001]
- Research Grants Council of Hong Kong Joint Research Scheme [21361162001]
- Chinese Academy of Sciences
- Technology Commission of Shanghai Municipality
- Croucher Foundation of Hong Kong
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The activated alkynes have been used successfully for the first time as the dipolarophile in the palladium-catalyzed asymmetric (3 + 2) cycloaddition, affording highly functionalized cyclopentenes in good to high yields with high chemoselectivities and good to high enantioselectivities. The introduction of an additional carbonyl group at the alpha-position of the alkynyl esters is the key to activating the carbon-carbon triple bond. The reaction process was investigated, and an inverse process of Pd-catalyzed (3 + 2) cycloaddition was observed.
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