Synthesis of planar chiral ferrocenyl 1,3-diamines and 1,3-amino ethers

被引:21
作者
Anderson, JC [1 ]
Blake, AJ [1 ]
Arnall-Culliford, JC [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
D O I
10.1039/b307014j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient syntheses of novel planar chiral 1,3-diamines and 1,3-amino ethers with an oxy or amino function directly bound to the cyclopentadienyl ring of ferrocene has been developed. The key reaction is the Cu2O promoted substitution of (pR)-N,N-diisopropyl-2-iodoferrocenecarboxamide with either phthalimide or AcOH to introduce nitrogen or oxygen functionality onto the cyclopentadienyl ring. The enantiomerically pure iodoferrocene derivative is available from the known enantioselective ortho-lithiation of N,N-diisopropylferrocenecarboxamide with n-BuLi-sparteine. In the course of these studies the synthesis of a novel C-2 symmetric C-2 dimer of N,N-dimethyl-1-ferrocenylethylamine was characterised by single crystal X-ray diffraction.
引用
收藏
页码:3586 / 3591
页数:6
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