Journal
ORGANIC LETTERS
Volume 21, Issue 6, Pages 1694-1698Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00251
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Funding
- National Natural Science Foundation of China [21572089]
- Program for Changjiang Scholars and the Innovative Research Team in Universities [PCSIRT: IRT_15R28]
- FRFCU [lzujbky-2018-61]
- Gansu Provincial Sci. & Tech. Department [2016B01017]
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A highly stereoselective synthesis of a spiro-cineole scaffold that contains four stereogenic centers from readily accessible 2-alkynylbenzaldehydes and styrenes under very mild reaction conditions was reported. This cascade reaction involves a Ag(I)-catalyzed alkyne cycloisomerization and oxa-[4 + 2]-cycloaddition to give an oxonium intermediate which subsequently undergoes a previously unexplored 1,2-alkyl migration to access highly strained spiro-2-oxabicyclo[2.2.2]octanes in high yields with excellent stereoselectivities.
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