37056-75-0Relevant articles and documents
Gold-Catalyzed Oxidative Aminocyclizations of Propargyl Alcohols and Propargyl Amines to Form Two Distinct Azacyclic Products: Carbene Formation versus a 3,3-Sigmatropic Shift of an Initial Intermediate
Chao, Tzu-Hsuan,Chen, Mu-Jeng,Liu, Rai-Shung,Raj, Antony Sekar Kulandai,Sasane, Amit Vijay
supporting information, p. 16932 - 16938 (2020/11/30)
Gold-catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o-biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron-rich gold catalysts lead only to gold carbenes, which can generate gold enolates or oxoarylation intermediates with enolate species having a barrier smaller than that of oxoarylation species.
Cu(II)-catalyzed enantioselective 1,3-dipolar cycloaddition of nitrones with α, β-unsaturated acyl phosphonates
Xie, Lei,Bai, Hui,Li, Jiaqi,Yu, Xuan,Zhang, Zhenhua,Fu, Bin
supporting information, p. 2923 - 2930 (2017/04/27)
A highly enantioselective 1, 3-dipolar cycloaddition of nitrone with α, β-unsaturated acyl phosphonate was developed for the first time by using a chiral indane-bis(oxazoline)-copper(II) complex. The reaction proceeded smoothly under mild conditions to provide isoxazolidines with multi-stereocenters in good yields with high to excellent diastereo- (>20:1 dr) and enantioselectivities (up to 99% ee). The resulting products were readily converted to multi-functional isoxazolidines or γ-amino alcohol compounds.
Rhodium-catalyzed cyclization of diynes with nitrones: A formal [2+2+5] approach to bridged eight-membered heterocycles
Wang, Chunxiang,Wang, Dongping,Yan, Hao,Wang, Haolong,Pan, Bin,Xin, Xiaoyi,Li, Xincheng,Wu, Fan,Wan, Boshun
supporting information, p. 11940 - 11943 (2015/01/09)
N-aryl-substituted nitrones were employed as fiveatom coupling partners in the rhodium-catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic C-H activation of the N-aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight-membered heterocycles with broad substrate scope. The results of this study may provide new insight into the chemistry of nitrones and find applications in the synthesis of other heterocycles,.