Journal
ORGANIC LETTERS
Volume 20, Issue 18, Pages 5835-5839Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02523
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Funding
- NSFC [21572087, 21632003]
- Key Program of Gansu Province [17ZD2GC011]
- 111 Program from the MOE of P. R. China
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A dearomative remote activation strategy for the asymmetric functionalization of benzylic C-H bonds of heteroaryl aldehydes under bifunctional Bronsted base catalysis has been developed. The in situ generated o-QDMs-type dienolate intermediates were efficiently and stereoselectively trapped by nitroolefins through an asymmetric Michael/nitro-aldol cascade reaction. Using this strategy, a wide variety of synthetically significant tetrahydrodibenzothiophene and tetrahydrodibenzofuran derivatives were synthesized in good yields with high enantioselectivities.
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