Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 23, Pages 14963-14970Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01782
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Funding
- National Natural Science Foundation of China [21702080]
- Natural Science Foundation of Jiangxi Province of China [20181BAB213003]
- Open Project Program of Key Laboratory of Functional Small Organic Molecule, Ministry of Education, Jiangxi Normal University [KLFS-KF-201603]
- foundation of Jiangxi Educational Committee [170223]
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The first highly enantioselective construction of chiral cyclopropa[c]coumarins was described. Using commercially available (bis)cinchona alkaloid (DHQ)(2)PYR as the chiral Lewis base catalyst, together with Cs2CO3 as the achiral base, the reaction of a series of coumarin-3-carboxylate and 3-benzoyl coumarins with tert-butyl 2-bromoacetate could give rise to the corresponding cyclopropa[c]coumarins bearing three continuous chiral stereocenters in 83-93% ee and 90-97% ee, respectively. The reaction is proposed to proceed via an in situ generated ammonium ylide intermediate.
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