New axially chiral atropos and tropos secondary diamines as ligands for enantioselective intramolecular hydroamination

被引:36
作者
Aillaud, Isabelle [1 ]
Wright, Karen [2 ]
Collin, Jacqueline [1 ]
Schulz, Emmanuelle [1 ]
Mazaleyrat, Jean-Paul [2 ]
机构
[1] Univ Paris 11, UMR 8182, ICMMO, Equipe Catalyse Mol, F-91405 Orsay, France
[2] Univ Versailles, UMR CNRS 8180, ILV, F-78035 Versailles, France
关键词
D O I
10.1016/j.tetasy.2007.11.029
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The highly constrained, axially chiral atropos diamines (R',S,S)-1, (R',R,R)-1 and (R',S,R)-1 and their tropos analogue (R')-2 have been prepared via bis-N,N-dialkylation of (R)-2,2'-diamino-1,1'-binaphthyl, using either (R)- or (S)-2,2'-bis(bromomethyl)-1,1'-binaphthyl and 2,2'-bis(bromomethyl)-1,1'-biphenyl as alkylating agents, followed by selective nickel chloride-catalysed bis(monohydrogenolysis) of the tertiary amino groups of the so-obtained (R',R,R)-4, (R',S,S)4, (R',R,)-4 and (R')-6, respectively, by lithium aluminium hydride in refluxing THF or THF/diglyme. The diamines (R',S,S)-1, (R',R,R)-1, (R',S,R)-1 and (R')-2 have been evaluated as ligands for ytterbium-catalysed intramolecular hydroamination and compared to the ligand 1,1'-binaphthyl-2,2'-bis(benzylamine) (R')-3. They afforded highly active catalysts for the cyclisation of aminopentenes and ammohexenes with up to 58% ee. (c) 2007 Elsevier Ltd. All rights reserved.
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页码:82 / 92
页数:11
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