The Regiocontrollable Enantioselective Synthesis of Chiral Trifluoromethyl-Containing Spiro-Pyrrolidine-Pyrazolone Compounds via Amino-Regulated 1,3-Proton Migration Reaction

Autor:	Zhenghao Dong, Mengmeng Sun, Kairong Wang, Yongzhen Li, Yifei Guo, Qushuo Chen, Fengyun Gao, Yabo Deng, Yalan Wang, Wenjin Yan
Rok vydání:	2021
Předmět:	Trifluoromethyl Pyrrolidines Molecular Structure Organic Chemistry Enantioselective synthesis Squaramide Pyrazolone Stereoisomerism Medicinal chemistry Pyrrolidine Cycloaddition Umpolung chemistry.chemical_compound Malonate chemistry medicine Spiro Compounds Protons Pyrazolones medicine.drug
Zdroj:	The Journal of organic chemistry. 86(18)
ISSN:	1520-6904
Popis:	An amino-controlled regiodivergent asymmetric synthesis of CF3-containing spiro-pyrrolidine-pyrazolone compounds is described. With alkaloid-derived squaramide as catalyst, the 1,3-dipolar cycloaddition of α,β-unsaturated pyrazolone with diethyl 2-((2,2,2-trifluoroethyl)imino) malonate offered adducts in excellent yields, dr, and ee. While the cyclohexanediamine-derived squaramide was employed, the reaction afforded a series of structure isomers through a switched umpolung reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3fba6754969311013285f319209f97d4 https://pubmed.ncbi.nlm.nih.gov/34494838 Zobrazit plný text záznamu