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Issue 27, 2020
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Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones

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Abstract

An anti-selective catalytic asymmetric Michael-type vinylogous addition of β,γ-butenolides to chromones was developed. The catalyst system developed herein is characterized by tuning of the steric and electronic effects using a proper Biphep-type chiral ligand to invert the diastereoselection, and improvement of the catalyst turnover by a coordinative phenolic additive. The catalytic protocol renders potentially biologically active natural product analogs accessible in good yield with moderate diastereoselectivity and high enantiomeric purity, mostly greater than 99% ee.

Graphical abstract: Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones

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Supplementary files

Article information


Submitted
03 Apr 2020
Accepted
20 Jun 2020
First published
22 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 7170-7176
Article type
Edge Article

Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones

J. Cui, N. Kumagai, T. Watanabe and M. Shibasaki, Chem. Sci., 2020, 11, 7170
DOI: 10.1039/D0SC01914C

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