“γ -支化烯丙胺的不对称氢化以高效合成γ -致氮胺”的决议书

IF 2.6 Q2 MULTIDISCIPLINARY SCIENCES Natural sciences (Weinheim, Germany) Pub Date : 2021-06-14 DOI:10.1002/ntls.10021/v1/decision1
Jian Zhang, Tiantian Chen, Yuanhao Wang, F. Zhou, Zhenfeng Zhang, I. Gridnev, Wanbin Zhang
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引用次数: 5

摘要

采用大咬角双膦- rh催化剂,通过对γ-支化n -邻苯二甲酰烯丙胺进行不对称加氢,实现了γ-氨基基胺的高效构建。具有不同类型γ-取代基的理想产物具有不定量收率和优异的对映选择性(高达>99.9% ee)。该方案为γ-氨基衍生物的制备提供了一种实用的方法,如著名的抗抑郁药物氟西汀(高达50000 S/C)。机理计算表明,在铑催化氢化反应中存在弱相互作用促进活化模式,这与传统的配位促进活化模式完全不同。
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Decision letter for "Asymmetric hydrogenation of γ ‐branched allylamines for the efficient synthesis of γ ‐chirogenic amines"
The efficient construction of γ-chirogenic amines has been realized via asymmetric hydrogenation of γ-branched N-phthaloyl allylamines by using a bisphosphine-Rh catalyst bearing a large bite angle. The desired products possessing different types of γ-substituents were obtained in quantitative yields and with excellent enantioselectivities (up to >99.9% ee). This protocol provided a practical method for the preparation of γ-chirogenic amine derivatives such as the famous antidepressant drug Fluoxetine (up to 50000 S/C). The mechanism calculation shows a weak interaction-promoted activation mode which is completely different from the traditional coordination-promoted activation mode in the Rh-catalyzed hydrogenation.
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