Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 3, Pages 358-368Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00549g
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Funding
- National Natural Science Foundation of China [21372002, 21232007, 81373398]
- PAPD
- Natural Science Foundation of Jiangsu Province [BK20160003]
- Graduate Students Project of JSNU
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The first catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols with enamines has been established, which afforded tetronic acid-derived diarylmethanes in considerable yields and good enantioselectivities (up to 89% yield, 98 :2 er). This reaction not only provided an efficient method for enantioselective synthesis of tetronic acid-derived diarylmethanes with biological relevance, but also fulfilled the task of developing catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols by using tetronic acid-derived enamines as competent nucleophiles. More importantly, the preliminary biological evaluation of some selected products revealed that this class of chiral tetronic acid-derived diarylmethanes exhibited strong cytotoxicity to HT-29, MCF-7 and TE-13 cancer cell lines.
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