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首页> 外文期刊>Chemistry: A European journal >Facile and Efficient Enantioselective Strecker Reaction of Ketimines by Chiral Sodium Phosphate
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Facile and Efficient Enantioselective Strecker Reaction of Ketimines by Chiral Sodium Phosphate

机译：手性磷酸钠对Ketimines的快速高效对映选择性Strecker反应

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摘要

A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol% BNPNa (BNP=1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol % para-test-butyl-ortho-adamantylphenol (PBAP) were introduced into the reaction, up to 96% yield and up to 95% ee (ee = enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from beta-acetonaphthone, alpha-indanone, and a-tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1'-binaphthy1-2,2'-diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications.
机译：已开发了一种手性碱金属盐催化的酮亚胺的简便高效对映选择性斯特雷克反应。当原位制备10 mol％的BNPNa（BNP = 1,1'-联萘基-2,2'-二基磷酸酯）和10 mol％的对测试丁基-正金刚烷基苯酚（PBAP）引入反应时，最高可达96得到％收率和高达95％的ee（ee ＝对映体过量）。发现脂族和芳族酮亚胺，特别是衍生自β-乙酰萘酮，α-茚满酮和α-四氢萘酮的空间上庞大的环状酮亚胺均适用于该反应。根据实验结果和先前的报道，尽管存在PBAP，三甲基甲硅烷基氰化物（TMSCN）仍被认为是真正的反应性亲核试剂，并提出了可能的工作模型来解释不对称诱导的起源。 1,1'-联萘1-2,2'-二基磷酸（BNPH）的易用性和操作的简便性对实际应用是有益的。

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