1685-19-4Relevant articles and documents
Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
supporting information, p. 4302 - 4306 (2021/02/16)
The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization
Li, Quanzhe,Liu, Jiaxin,Wei, Yin,Shi, Min
supporting information, p. 2438 - 2455 (2020/01/31)
A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.
Copper-catalyzed tandem annulation/enol nucleophilic addition to access multisubstituted indoles
Song, Wangze,Li, Ming,He, Junnan,Li, Junhao,Dong, Kun,Zheng, Yubin
supporting information, p. 2663 - 2669 (2019/03/13)
A method to access various multisubstituted indoles from propargylic alcohols and readily available enol nucleophiles by copper-catalyzed tandem annulation/enol nucleophilic addition has been developed. Compared to the expensive metal catalysts such as platinum, gold, silver, and palladium used previously, the most economical copper(i) catalyst could achieve this reaction efficiently. The fused heterocyclic compounds, pyrrolo[1,2-a] indoles, could be afforded by further transformation of the products. The allyl cation intermediate may be involved in the mechanism.