An Asymmetric Nitro-Mannich Reaction Applicable to Alkyl, Aryl, and Heterocyclic Imines

Autor:	Gareth P. Howell, Ron M. Lawrence, C. Wilson, James C. Anderson
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Aldimine Aryl Organic Chemistry Chiral ligand Enantioselective synthesis General Medicine Catalysis chemistry.chemical_compound chemistry Heterocyclic compound Organic chemistry Enantiomeric excess Mannich reaction Alkyl
Zdroj:	The Journal of Organic Chemistry. 70:5665-5670
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo050762i
Popis:	[reaction: see text] A protocol for the enantioselective nitro-Mannich coupling between alkyl, aryl, and heterocyclic p-methoxybenzylimines and trimethylsilylnitropropanate catalyzed by a chiral tBu-BOX Cu(II) catalyst is described. It uses the lowest reported loading of commercially available metal catalyst and chiral ligand, and gives the highest yields and selectivities for a broad substrate range including nonaromatic aldimines. The resultant beta-nitroamines are obtained in 70-94% enantiomeric excess in good yield and can be readily reduced to synthetically useful 1,2-diamines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f3420e07ac8af5ee6dc37d2978892fa0 https://doi.org/10.1021/jo050762i Zobrazit plný text záznamu