Synthesis of chiral primary 1-ferrocenylalkylamines via highly diastereoselective addition of organolithium compounds to ferrocenecarboxaldehyde imine derived from (S)-2-methoxy-1-phenylethylamine

被引:30
作者
Fukuda, T [1 ]
Takehara, A [1 ]
Haniu, N [1 ]
Iwao, M [1 ]
机构
[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 8528521, Japan
关键词
D O I
10.1016/S0957-4166(00)00398-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The imine 3 derived from ferrocenecarboxaldehyde 1 and (S)-2-methoxy-1-phenylethylamine 2 was reacted with several organolithium compounds to give 1,2-addition products 4 in good yields with excellent diastereoselectivities (>98% de). The adducts 4 were readily converted to the corresponding primary 1-ferrocenylalkylamines 5 by hydrogenolysis or stereoretentive substitutions without racemization. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码:4083 / 4091
页数:9
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