1-Phosphanorbornadiene-imines and amines in enantioselective allylic C- and N-alkylation

Autor:	François Mathey, François Mercier, Franck Brebion, Romain Dupont
Rok vydání:	2003
Předmět:	Allylic rearrangement Organic Chemistry Enantioselective synthesis Alkylation Dimethyl malonate Catalysis Inorganic Chemistry Reaction rate chemistry.chemical_compound Benzylamine Enantiopure drug chemistry Organic chemistry Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry. 14:3137-3140
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(03)00591-3
Popis:	The reaction of enantiopure 2-formyl-1-phosphanorbornadiene 3 with primary amines at room temperature in the presence of an acid catalyst gives the corresponding enantiopure imines 4-7 in quantitative yields. These imines are efficient ligands for the palladium-catalyzed enantioselective allylic C- and N- alkylations of dimethyl malonate and benzylamine by 1,3-diphenylprop-2-enyl acetate with ee's as high as 93 and 86–90%, respectively, and high reaction rates at room temperature (1 and 3 h, respectively, for quantitative conversions).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::49ea27993be3bfb0d0e13276ec632e15 https://doi.org/10.1016/s0957-4166(03)00591-3 Zobrazit plný text záznamu Full Text from ScienceDirect