Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 17, Pages 4606-4611Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00820c
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Funding
- National Natural Science Foundation of China [22101161]
- Natural Science Foundation of Shanxi [201901D111081, 20210302124213]
- Fund Program for the Scientific Activities of Selected Returned Overseas Professionals in Shanxi Province
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Phosphine-catalyzed reactions enable efficient synthesis of polysubstituted olefins or multifunctional dienes. The study reveals the divergent reactivity of alkynoates toward electrophiles under organophosphine catalysis.
Phosphine-catalyzed chemoselective acylesterification, tandem addition and Michael type reaction between alkynoates and acid anhydrides have been developed, which lead to efficient synthesis of either the polysubstituted olefins or the multifunctional dienes in moderate to excellent yields with high stereoselectivity. Mechanistic investigation indicates that the tandem addition proceeds via a Michael-umpolung addition cascade. This study unveils the divergent and unprecedented reactivity of alkynoates toward C-O bond of electrophiles under the organophosphine catalysis.
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