Issue 3, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
14 ذو الحجة 1437
Accepted
10 ربيع الأول 1438
First published
13 ربيع الأول 1438

Org. Chem. Front., 2017,4, 358-368

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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