Kinetic resolution of primary allylic amines via palladium-catalyzed asymmetric allylic alkylation of malononitriles

Kinetic resolution of primary allylic amines via palladium-catalyzed asymmetric allylic alkylation of malononitriles
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通过钯催化丙二腈的不对称烯丙基烷基化动力学拆分烯丙伯胺

DOI:
10.1039/c5ob00671f
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发表时间:
2015
影响因子:
3.2
通讯作者:
Tian Shi-Kai
Tian Shi-Kai
中科院分区:
化学3区
文献类型:
--
作者:
Wang Yong;Xu Ya-Nan;Fang Guo-Sheng;Kang Hong-Jian;Gu Yonghong;Tian Shi-Kai

文献摘要

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通过[Pd(allyl)Cl]2/(S)-BINAP催化和均三甲苯磺酰肼加速的丙二腈的不对称烯丙基烷基化反应,在有氧条件下拆分了一系列烯丙基伯胺,选择性因子高达491。此外,该反应还可用于不对称合成高纯度的α-支链烯丙基取代丙二腈。
A range of primary allylic amines were resolved with selectivity factors of up to 491 through [Pd(allyl)Cl]2/(S)-BINAP-catalyzed and mesitylsulfonyl hydrazide-accelerated asymmetric allylic alkylation of malononitriles involving enantioselective C–N bond cleavage under aerobic conditions. Moreover, the reaction proved useful for the asymmetric synthesis of α-branched allyl-substituted malononitriles with high enantiopurity.