A Continuously Regenerable Chiral Ammonia Borane for Asymmetric Transfer Hydrogenations

Angewandte Chemie
Qiwen ZhouHaifeng Du

Abstract

A novel chiral ammonia borane was designed and developed through the dehydrogenation of ammonia borane with a chiral phosphoric acid, which was highly effective for the asymmetric transfer hydrogenation of imines and β-enamino esters to afford high levels of reactivities and enantioselectivities. Significantly, this chiral ammonia borane can be continuously regenerated during the transfer hydrogenation with the assistance of water and ammonia borane, which made it possible to obtain satisfactory results using only 0.1 mol % of the chiral phosphoric acid. Notably, the role of chiral phosphoric acid is to produce the chiral ammonia borane.

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Citations

May 8, 2019·Angewandte Chemie·Michael DömlingHolger Braunschweig
Apr 10, 2019·Chemistry : a European Journal·Devin H A BoomJ Chris Slootweg
Aug 24, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Obaid H HashmiMarc Visseaux
Sep 26, 2020·Organic & Biomolecular Chemistry·Chiara FaverioMaurizio Benaglia
Jun 11, 2020·Chemistry : a European Journal·Coralie GelisFrank Glorius
Apr 3, 2020·Organic Letters·Kodai SaitoTakahiko Akiyama
Aug 24, 2019·Journal of the American Chemical Society·Travis LundriganAlexander W H Speed
Dec 7, 2018·Journal of the American Chemical Society·Maialen Espinal-ViguriRuth L Webster
Nov 13, 2021·Chemical Communications : Chem Comm·Xinying LiXuenian Chen

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