(S,S)N,N'-双(对氯-α-异丙基苄基)-1,10-二氮杂-18-冠-6的合成及其应用

Synthesis of (S, S) N, N＇ -Bis-(p-chloro-a-isopropyl-benzyl)-1, 10-diaza-18-crown-6 and its Application

手性冠醚被用作不对称合成的手性试剂,或者成为具有构型识别能力的主体,它们已成为冠醚化学中的一个引人注目的领域。近年来,也有一些关于含氮手性冠醚的报道,但大多数以氨基酸为基本原料。

(S)-(-) 4-Chloro-a-isopropyl benzylamine was used as chiral block. With 1,8- dichlor-3, 6-dichlorooctanc, it afforded (S, S) 3, 6-dioxo-1, 8- bis N, N-p- chloro-a-isop- ropylbenzyl) octanediamine which, upon further reaction with 3,6- dioxo-1,8-octancdioyl chloride, gave the corresponding cyclic diamide. Upon reduction with lithium aluminium hydride of the cyclic diamide, the title crown ether was obtained. Its ammonium thiocyanate complex was also prepared. A copper salt with the crown ether was used as a catalyst of cyclopropnation of 2, 5-dimethylhexadiene-2, 4. The yield of the chrysanthemic ester was significantly improved, but no asymmetric induction was observed.