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Issue 3, 2017
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Catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols with tetronic acid-derived enamines: enantioselective synthesis of tetronic acid-derived diarylmethanes

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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.

Graphical abstract: Catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols with tetronic acid-derived enamines: enantioselective synthesis of tetronic acid-derived diarylmethanes

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Article information


Submitted
15 Sep 2016
Accepted
09 Dec 2016
First published
12 Dec 2016

Org. Chem. Front., 2017,4, 358-368
Article type
Research Article

Catalytic asymmetric substitution of ortho-hydroxybenzyl alcohols with tetronic acid-derived enamines: enantioselective synthesis of tetronic acid-derived diarylmethanes

M. Xu, H. Wang, Y. Wan, G. He, J. Yan, S. Zhang, S. Wang and F. Shi, Org. Chem. Front., 2017, 4, 358
DOI: 10.1039/C6QO00549G

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