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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).… Click to show full abstract
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.
Journal Title: Organic chemistry frontiers
Year Published: 2017
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