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γ-手性顺式的共轭烯醛与有机锂化合物的立体选择性反应

Diastereoselective Reactions of Chiral γ-Amino Z-Enals with Organolithium Compounds

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【作者】 王钒

【Author】 WANG Fan(Department of Applied Chemistry, Jiangsu Institute of Petrochemical Technology, 213016 Changzhou, Jiangsu)

【机构】 江苏石油化工学院应用化学系 江苏常州 213016

【摘要】 本文研究了在手性的顺式-γ-氨基-α,β-不饱和醛(7)与有机锂化合物的亲核加成反应中的1,4-不对称诱导效应。结果表明:7与α-烷氧基乙烯醇锂类化合物的反应导致了优良的非对映立体选择性(d.e.:60~90%),而与烷基锂试剂的反应也给出了高度的立体选择性(d.e.:74~86%)。这说明在这些反应中,存在着一种1,4-不对称诱导效应。

【Abstract】 The possibility of 1,4-asymmetric induction in some nucleophilic addition reactions of chiral γ-amino Z-enals 7 with organolithium compounds was investigated. The reactions of lithium enolates with 7 led to good diastereoselectivities (d. e.: 60- 90%), and high level of diastereoselectivities (d. e: 74- 86%) was also observed in the corresponding reactions of alkyllithium. This means that a novel remote 1,4-asymmetric induction results in these reactions.

  • 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,1995年02期
  • 【分类号】O621.25
  • 【下载频次】86
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