76866-96-1Relevant articles and documents
Copper(i)/Lewis acid triggered ring-opening coupling reaction of cyclopropenes with nitriles
Huang, Huawen,Ji, Xiaochen,Xiao, Fuhong,Deng, Guo-Jun
, p. 26335 - 26338 (2015/10/20)
A ring-opening coupling reaction of D-A cyclopropenes and nitriles is described for the facile synthesis of γ-amino ketones. The co-catalytic system combining copper(i) and boron trifluoride would be inspiring because it disfavors the [3 + 2] cycloadditio
Rhodium(III)-Catalyzed [3+2] Annulation of 5-Aryl-2,3-dihydro-1H-pyrroles with Internal Alkynes through C(sp2)-H/Alkene Functionalization
Zhou, Ming-Bo,Pi, Rui,Hu, Ming,Yang, Yuan,Song, Ren-Jie,Xia, Yuanzhi,Li, Jin-Heng
supporting information, p. 11338 - 11341 (2016/02/19)
This study describes a new rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp2)-H bond and addition/protonolysis of an alkene C=C bond. This method is applicable to a wide range of 5-aryl-2,3-dihydro-1H-pyrroles and internal alkynes, and results in the assembly of the spiro[indene-1,2′-pyrrolidine] architectures in good yields with excellent regioselectivities.
Organometallic Ring-Opening Reactions of N-Acyl and N-Alkoxycarbonyl Lactams. Synthesis of Cyclic Imines
Giovannini, Arianna,Savoia, Diego,Umani-Ronchi, Achille
, p. 228 - 234 (2007/10/02)
The reactions of hexyl- and phenylmagnesium bromides with N-acyl and N-alkoxycarbonyl lactams in tetrahydrofuran at -78 deg C have been performed to determine the factors affecting the regioselectivity.N-Pivaloyl γ- and δ-lactams undergo the ring-opening reactions with both Grignard reagents, whereas on the N-benzoyl γ-lactam a complete selectivity is achieved only with phenylmagnesium bromide.The N-Cbz γ- and δ-lactams preferentially react at the exocyclic carbonyl group, especially with hexylmagnesium bromide.The N-Boc five- to eight-membered lactams undergo the ring-opening reaction to give N-Boc-ω-amino ketones, although the efficiency slightly decreases by increasing the ring size.The deprotection of the N-Boc-ω-amino ketones with trifluoroacetic acid easily affords the corresponding five- to seven-membered cyclic imines.Pyridine alkaloids containing the cyclic imine moiety have been prepared by a modified route, exploiting the more easily available pyridyllithium reagents, instead of the corresponding Grignard reagents.