Doubly stereocontrolled asymmetric Michael addition of acetylacetone to nitroolefins promoted by an isosteviol-derived bifunctional thiourea

Autor:	Jing-Chao Tao, Yu-Xia Liu, Zhi-wei Ma, Li-juan Huo, Xiang Gao
Rok vydání:	2012
Předmět:	Inorganic Chemistry chemistry.chemical_compound chemistry Thiourea Acetylacetone Organic Chemistry Michael reaction Organic chemistry Physical and Theoretical Chemistry Bifunctional Medicinal chemistry Catalysis Adduct
Zdroj:	Tetrahedron: Asymmetry. 23:443-448
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2012.03.020
Popis:	A novel class of chiral bifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a tertiary amino group was designed and prepared. The thioureas were proven to be effective for catalyzing the doubly stereocontrolled asymmetric Michael addition between acetylacetone and nitroolefins. The corresponding adducts were obtained in high yields (up to 95%) and with good to excellent enantioselectivities (up to 97%). In addition, the reaction of tert -butyl acetoacetate and trans -β-nitrostyrene also proceeded smoothly with good enantioselectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::109cb4d6ffb336ba38c4ca58cd3cd24f https://doi.org/10.1016/j.tetasy.2012.03.020 Zobrazit plný text záznamu Full Text from ScienceDirect