Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides

Autor:	Mei-Xin Zhao, Juan Xiang, Zi-Qiang Zhao, Xiao-Li Zhao, Min Shi
Rok vydání:	2020
Předmět:	Silver nitrate chemistry.chemical_compound chemistry Cascade reaction Organic Chemistry Enantioselective synthesis Para-quinone Transesterification Physical and Theoretical Chemistry Biochemistry Combinatorial chemistry Catalysis Stereocenter
Zdroj:	Organic & Biomolecular Chemistry. 18:1637-1646
ISSN:	1477-0539 1477-0520
DOI:	10.1039/c9ob02652e
Popis:	A catalytic asymmetric synthesis of 3,4-dihydrocoumarins with adjacent tertiary–quaternary stereocenters by 1,6-addition/transesterification cascade reaction of α-isocyanoacetates with ortho-hydroxyphenyl-substituted para-quinone methides (p-QMs) has been developed. Using a combination of dihydroquinidine-derived aminophosphine and silver nitrate as a binary catalytic system, moderate to good yields, excellent diastereoselectivities (>20 : 1 dr) and good to excellent enantioselectivities (up to 94% ee) were achieved for a wide range of isocyanoacetates and p-QMs.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ab5526fba298eb4afe84a7f3e1c15863 https://doi.org/10.1039/c9ob02652e Zobrazit plný text záznamu