1736-31-8Relevant articles and documents
Three-component domino process for the pyrrolizine skeleton via [3 + 2]-cycloaddition-enamine cyclization triggered by a gold catalyst
Sugimoto, Kenji,Yamamoto, Nozomi,Tominaga, Daisuke,Matsuya, Yuji
, p. 1320 - 1323 (2015)
Pyrrolizines are bicyclic fused azaheterocycles with a bridgehead nitrogen contained in a core skeleton and are often found in biologically active compounds. Despite their importance, there have been few reports on concise and flexible syntheses of pyrrolizines. A novel one-pot, convergent method is described for pyrrolizines by simple mixing of iminoesters, acetylenes, and dipolarophiles in the presence of a cationic gold catalyst and an acid additive. This domino process affords multisubstituted pyrrolizines without handling unstable intermediates.
Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
Mimura, Shohei,Mizushima, Sho,Sawamura, Masaya,Shimizu, Yohei
, p. 537 - 543 (2020/05/14)
A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. Opposite enantiomers were obtained from (Z)- and (E)-isomers, with a higher enantiomeric excess from the (Z)-isomer.
Metal-Free Oxidative [5+1] Cyclization of 1,5-Enynes for the Synthesis of Pyrazine 1-Oxide
Xia, Xiao-Feng,Zhao, Mingming,He, Wei,Zou, Lianghua,San, Xinxin,Wang, Dawei
supporting information, p. 3621 - 3626 (2020/08/05)
A chemo-selective nitrosylation of 1,5-enynes via a sequence of NO radical incorporation and intramolecular radical cyclization was reported. The formation of two C?N bonds and one C?O bond make this [5+1] cycloaddition reaction an efficient approach to synthesize pyrazine 1-oxides in moderate to good yields. Metal-free, short reaction time and mild conditions render this strategy more practical, eco-friendly and convenient. Synthetic utility of this protocol is highlighted by scaffolds diversification. (Figure presented.).