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

Chemical Science
Jin CuiMasakatsu Shibasaki

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.

References

Jul 18, 2001·Journal of the American Chemical Society·N YoshikawaM Shibasaki
May 14, 2009·Accounts of Chemical Research·Masakatsu ShibasakiNaoya Kumagai
Dec 10, 2009·Journal of the American Chemical Society·Mitsutaka IwataMasakatsu Shibasaki
Apr 27, 2010·Chemical Society Reviews·Barry M Trost, Cheyenne S Brindle
Mar 23, 2011·Journal of the American Chemical Society·Mitsutaka IwataMasakatsu Shibasaki
Apr 27, 2011·Angewandte Chemie·Naoya Kumagai, Masakatsu Shibasaki
May 3, 2014·Angewandte Chemie·Karin WeidnerMasakatsu Shibasaki
Jun 24, 2017·Chemical Reviews·Bin MaoBen L Feringa
Jul 12, 2017·The Journal of Organic Chemistry·Akinobu MatsuzawaMasakatsu Shibasaki
Jan 10, 2018·Chemistry : a European Journal·Jin CuiMasakatsu Shibasaki
Apr 24, 2018·The Journal of Organic Chemistry·Toshifumi TakeuchiMasakatsu Shibasaki
May 31, 2018·Chemical Society Reviews·Yasuhiro YamashitaShū Kobayashi
Jan 16, 2019·Journal of the American Chemical Society·Barry M TrostJacob S Tracy

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BETA
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