Catalytic asymmetric mannich-type reaction of N-alkylidene-α-aminoacetonitrile with ketimines

Angewandte Chemie
Shaoquan LinMasakatsu Shibasaki

Abstract

Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Brønsted base cooperative catalyst allows for an efficient stereoselective coupling of N-alkylidene-α-aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra- and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol % catalyst loading.

References

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Citations

Feb 3, 2016·Chemistry : a European Journal·Shaoquan LinMasakatsu Shibasaki
Oct 31, 2017·Organic & Biomolecular Chemistry·Saumen HajraAtanu Hazra
Aug 9, 2016·Chemical Communications : Chem Comm·Raquel de la CampaDarren J Dixon
Nov 8, 2017·Angewandte Chemie·Taichi KanoKeiji Maruoka
Sep 22, 2015·Angewandte Chemie·Rosa López, Claudio Palomo
May 19, 2018·Journal of the American Chemical Society·Xinxin ShaoSteven J Malcolmson

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