B(C6F5)3: A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals

Organic Letters
Jia-Hui ZhouTeck-Peng Loh

Abstract

Lewis acid B(C6F5)3 catalyzed the Diels-Alder reactions of multisubstituted open-chain dienes and α,β-enals to afford the desired products with high exo-selectivities are reported. The substituent effect of the dienes and dienophiles on the product's stereoselectivity was thoroughly investigated, and it was found that most of the desired exo-Diels-Alder products could be obtained in good yields and with high exo-stereoselectivities.

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Citations

Jan 23, 2016·Journal of the American Chemical Society·Zengjin LiuZhenlei Song
Jul 12, 2016·The Journal of Organic Chemistry·Jeffrey ButerAdriaan J Minnaard
Sep 15, 2016·The Journal of Organic Chemistry·Hossay AbasAlan C Spivey
May 3, 2018·Chemistry, an Asian Journal·Bin Rao, Rei Kinjo
Aug 25, 2018·Chemical Communications : Chem Comm·Ryosuke HaraguchiShin-Ichi Fukuzawa

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