Journal
ORGANIC LETTERS
Volume 19, Issue 21, Pages 5892-5895Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02883
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Funding
- National Natural Science Foundation of China [21472028]
- National Key Technologies RD Program [2014BAD23B01]
- Thousand Talent Plan of Guizhou Province
- Guizhou University
- Singapore National Research Foundation [NRF-NRFI2016-06]
- Ministry of Education of Singapore [MOE2013-T2-2-003, MOE2016-T2-1-032]
- A*STAR Individual Research Grant (AME Domain)
- Nanyang Technological University
- 10 Talent Plan (Shicengci) of Guizhou Province
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A highly enantioselective method for quick access to dihydrocoumarins is reported. The reaction involves a cooperative catalytic process with carbene and in situ generated Bronsted acid as the catalysts. alpha-Chloro aldehyde and readily available and stable o-hydroxybenzhydryl amine substrates were used to generate reactive azolium ester enolate and ortho-quinone methide (o-QM) intermediates, respectively, to form dihydrocoumarins with exceptionally high diastereo- and enantioselectivities. The catalytic reaction products can be easily transformed to valuable pharmaceuticals and bioactive molecules.
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