Preparation of diamines by lithiation-substitution of imidazolidines and pyrimidines
Preparation of diamines by lithiation-substitution of imidazolidines and pyrimidines
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DOI：
10.1039/b301502e
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发表时间：
2003-05-07
影响因子：
3.2
通讯作者：
Howard, S
中科院分区：
文献类型：
--
作者：
Ashweek, NJ;Coldham, I;Howard, S
以未取代的二胺为原料，通过N-叔丁氧羰基（Boc）取代的咪唑烷合成了手性1，2-二胺和1，3-二胺（四氢咪唑）和嘧啶（六氢-1，3-二嗪），其用仲丁基锂处理以实现N-Boc基团的α-去质子化，然后加入亲电试剂，得到取代的产物，该产物可在酸性条件下水解，得到取代的1，2-或1，3-二胺。使用手性配体（-）-鹰爪豆碱促进咪唑烷底物的不对称去质子化，水解后得到对映体富集的1，2-二胺。
The synthesis of chiral 1,2-diamines and 1,3-diamines was achieved from the unsubstituted diamines by way of N-tert-butoxycarbonyl (Boc) substituted imidazolidines (tetrahydroimidazoles) and pyrimidines (hexahydro-1,3-diazines), which were treated with sec-butyllithium to effect deprotonation alpha- to the N-Boc group, followed by addition of an electrophile to give substituted products that could be hydrolysed under acidic conditions to give the substituted 1,2- or 1,3-diamines. Use of the chiral ligand (-)-sparteine promoted asymmetric deprotonation of the imidazolidine substrates to give, after hydrolysis, enantiomerically enriched 1,2-diamines.