26653-39-4Relevant academic research and scientific papers
Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes
Khrakovsky, Dimitri A.,Tao, Chuanzhou,Johnson, Miles W.,Thornbury, Richard T.,Shevick, Sophia L.,Toste, F. Dean
supporting information, p. 6079 - 6083 (2016/05/19)
The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer. Chiral allylic azides and amines are obtained by enantioselective hydroazidation and hydroamination of allenes catalyzed by acyclic diaminocarbene gold(I) catalysts derived from BINAM. The sense of enantioinduction is reversed for the two different nucleophiles, allowing easy access to both enantiomers with a single catalyst enantiomer.
Kinetics and mechanism of the racemization of aryl allenes catalyzed by cationic gold(i) phosphine complexes
Harris, Robert J.,Nakafuku, Kohki,Widenhoefer, Ross A.
supporting information, p. 12245 - 12254 (2015/03/31)
The kinetics of the racemization of aromatic 1,3-disubstituted allenes catalyzed by gold phosphine complexes has been investigated. The rate of gold-catalyzed allene racemization displayed first-order dependence on allene, and catalyst concentration and k
Copper-catalyzed regio- and stereoselective intermolecular three-component oxyarylation of allenes
Itoh, Taisuke,Shimizu, Yohei,Kanai, Motomu
supporting information, p. 2736 - 2739 (2014/06/09)
A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereoselectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.
Gold(I)-catalyzed stereoconvergent, intermolecular enantioselective hydroamination of allenes
Butler, Kristina L.,Tragni, Michele,Widenhoefer, Ross A.
supporting information; experimental part, p. 5175 - 5178 (2012/07/27)
Gold and silver: A 1:2 mixture of [{(S)-1}(AuCl)2] and AgBF 4 catalyzes the enantioselective hydroamination of chiral, racemic 1,3-disubstituted allenes with N-unsubstituted carbamates to form N-allylic carbamates in good yield, with high regio- and diastereoselectivity, and up to 92% ee (see scheme, Cbz=benzyloxycarbonyl). Copyright
