Enantioselective aza-Diels–Alder reaction of Brassard’s diene with aldimines catalyzed by chiral N,N′-dioxide–Yb(OTf)3 complex

Autor:	Zhenling Chen, Lili Lin, Xiaohua Liu, Xiaoming Feng, Donghui Chen, Jiangting Li
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Aldimine Diene Stereochemistry Organic Chemistry Enantioselective synthesis Reaction intermediate Biochemistry Medicinal chemistry Catalysis Brassard's diene chemistry.chemical_compound chemistry Drug Discovery Aza-Diels–Alder reaction
Zdroj:	Tetrahedron Letters. 51:3088-3091
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2010.04.009
Popis:	The chiral N , N′ -dioxide–Yb(OTf) 3 complex-catalyzed enantioselective aza-Diels–Alder reaction of Brassard’s diene with aldimines has been developed, giving the corresponding α,β-unsaturated δ-lactam derivatives in moderate yields with good enantioselectivities (up to 81% ee and up to 99% ee by single recrystallization) under mild conditions. Isolation of the reaction intermediate indicates that this asymmetric aza-Diels–Alder reaction proceeds through a stepwise Mannich-type pathway.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e3c956a51baa16f882468870f95195f8 https://doi.org/10.1016/j.tetlet.2010.04.009 Zobrazit plný text záznamu Full Text from ScienceDirect