Bifunctional Primary Amine-Squaramide Catalyzed Enantioselective Intramolecular Michael Addition of Keto-enones: A Convenient Process to the Stereocontrolled Construction oftrans-Dihydrobenzofuran Skeletons

Autor:	Zhenghong Zhou, Aidang Lu, Haibin Song, Yunting Liu, Keling Hu, Chuchi Tang, Youming Wang
Rok vydání:	2013
Předmět:	chemistry.chemical_compound Primary (chemistry) Chemistry Stereochemistry Intramolecular force Organic Chemistry Enantioselective synthesis Michael reaction Squaramide Amine gas treating Physical and Theoretical Chemistry Bifunctional Catalysis
Zdroj:	European Journal of Organic Chemistry. 2013:4836-4843
ISSN:	1434-193X
DOI:	10.1002/ejoc.201300331
Popis:	A highly diasterero- and enantioselective intramolecular Michael addition of keto-enones has been realized. By using the (R,R)-1,2-diphenylethane-1,2-diamine-based bifunctional primary amine-squaramide catalyst, the reaction proceeded smoothly to generate the corresponding trans-2,3-disubstituted dihydrobenzofuran derivatives in excellent yields with good to excellent diastereo- and enantioselectivities (up to 97:3 dr, up to >99 % ee).
Databáze:	OpenAIRE
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