875535-33-4Relevant articles and documents
Direct Catalytic Asymmetric Addition of Acetonitrile to Aldimines
Saito, Akira,Kumagai, Naoya,Shibasaki, Masakatsu
, p. 8187 - 8190 (2019/09/07)
Despite significant advances in catalytic asymmetric reactions with decent stereocontrol, those using acetonitrile as a pronucleophile are often disregarded due to their low reactivity and insufficient enantioselectivity. Herein we report the resurgence of this reaction in the chemical toolbox with high enantioselectivity (avg. > 95% ee). The combined use of a Ni(II) complex ligated with a chiral biscarbene and tBuOK engages acetonitrile in the catalytic generation of an α-cyanocarbanion and subsequent highly enantioselective addition to aldimines.
Catalytic enantioselective reaction of α-phenylthioacetonitriles with imines using chiral bis(imidazoline)-palladium catalysts
Kondo, Masaru,Kobayashi, Natsumi,Hatanaka, Tsubasa,Funahashi, Yasuhiro,Nakamura, Shuichi
, p. 9066 - 9070 (2015/06/16)
The catalytic enantioselective reaction of α-phenylthioacetonitriles with imines has been developed. The reaction of various imines proceeds in good yields and diastereo- and enantioselectivities in the presence of chiral bis(imidazoline)-palladium cataly
Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization
Ragoussi, Maria-Eleni,Walker, Stephen M.,Piccanello, Andrea,Kariuki, Benson M.,Horton, Peter N.,Spencer, Neil,Snaith, John S.
scheme or table, p. 7347 - 7357 (2011/02/16)
A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto α,β-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2
