The catalytic acylcyanation of imines

Chemistry, an Asian Journal
Subhas Chandra Pan, Benjamin List

Abstract

The catalytic acylcyanation of aldimines with acylcyanides and a direct three-component variant involving the generation of an imine in situ have been developed. Furthermore, a highly enantioselective version has been established, culminating in the first organocatalytic asymmetric three-component Strecker reaction. Jacobsen thiourea catalysts were found to catalyze the reaction with excellent enantioselectivities, whereas binol phosphates (binol = 1,1'-bi-2,2'-naphthol) proved to be catalytically active but only modestly enantioselective. A large number of different substrates could be used in the processes described, thus illustrating the potential of our reaction for the generation of diversity within the attractive alpha-amino carbonyl framework. Furthermore, a novel cyclic amidine was obtained from the reaction of acetyl cyanide with ketimines.

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Citations

May 23, 2015·Chemical Reviews·Nathalie BusschaertPhilip A Gale
May 14, 2009·Angewandte Chemie·Pilar García-GarcíaBenjamin List
Jan 3, 2013·Angewandte Chemie·Manuel Mahlau, Benjamin List
Nov 30, 2012·Angewandte Chemie·Katrien Brak, Eric N Jacobsen
Mar 25, 2016·Organic Letters·Hiroaki MurayamaMasaya Sawamura
Nov 19, 2009·Chemical Communications : Chem Comm·Jérôme Lacour, Delphine Moraleda
Jan 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Franz SteppelerJacek Wojaczyński
Jan 30, 2020·Chemistry : a European Journal·Tatsuhiko YoshinoShigeki Matsunaga
Apr 14, 2012·Chemical Communications : Chem Comm·You-Dong Shao, Shi-Kai Tian
Sep 28, 2013·The Journal of Organic Chemistry·Manabu HatanoKazuaki Ishihara
Jun 30, 2019·Organic Letters·Stephen W LawsJared T Shaw
Jul 7, 2015·Chemical Reviews·Thomas JamesBenjamin List

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