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有机化学
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有机化学 ›› 1994, Vol. 14 ›› Issue (2): 181-184. 上一篇    下一篇

研究论文

手性酒石酸二酰胺配体的合成及其锡络合物与苯甲醛的不对称加成

谭万会;张三奇;张生勇;冯锐   

  1. 陕西省化学研究所;第四军医大学化学教研室;中国军事医学科学院
  • 发布日期:1994-04-25

Synthesis of chiral diamide ligands of tartaric acid and asymmetric addition of their tin complexes with benzaldehyde

ZHANG SANQI;ZHANG SHENGYONG;FENG RUI   

  • Published:1994-04-25

被引次数

7

通过酒石酸乙酯和不同胺的酰胺化, 相应地合成到(+)N,N'-二苯基酒石酸二酰胺(2), (+)N,N'-二苄基酒石酸二酰胺(3),(+)N,N'-二环己基酒石酸二酰胺(4)和(+)N,N'-二正辛基酒石酸二酰胺(5).氯化亚锡与2当量的酒石酸二酰胺反应, 再加入烯丙基溴可制得手性锡络合物6, 锡络合物与苯甲醛反应,得到光学活性的高烯丙基化合物, 产率42～64％ , e.e.值24～62％.

关键词: 苯甲醛, 锡络合物, 酒石酸二酰胺配体, 手性试剂, 不对称反应

(+)-N,N'-diphenyl tartaric acid diamide 2, (+)-N,N'-dibenzyl tartaric acid diamide 3, (+)-dicyclohexyl tartaric acid diamide 4, and (+)-N,N'-di-n-octyl tartaric acid diamide 5 are synthesized via the amidate of diethyl tartarate and corresponding amine, respectively. Chiral tin complexes 6 are also prepared by treatment of tin dichloride with 2 equiv. of doubly deprotonated tartaric acid diamide followed by addition of an allylic bromide. The reaction of 6 with benzaldehyde affords optically active homoallyic alcohols in 42～64％ yield and in 24～62％ e.e..

Key words: TIN COMPLEX, BENZALDEHYDE, CHIRAL REAGENT

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