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Asymmetric Hydrogenation of γ-Branched Allylamines for the Efficient Synthesis of γ-Chirogenic Amines
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  • Jian Zhang,
  • Yuanhao Wang,
  • Fengfan Zhou,
  • Zhenfeng Zhang,
  • Ilya Gridnev,
  • Wanbin Zhang
Jian Zhang
Shanghai Jiao Tong University
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Yuanhao Wang
Shanghai Jiao Tong University
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Fengfan Zhou
Shanghai Jiao Tong University
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Zhenfeng Zhang
Shanghai Jiao Tong University
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Ilya Gridnev
Tohoku University
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Wanbin Zhang
Shanghai Jiao Tong University
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Abstract

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.

Peer review status:UNDER REVIEW

18 Mar 2021Submitted to Natural Sciences
19 Mar 2021Submission Checks Completed
19 Mar 2021Assigned to Editor
21 Mar 2021Reviewer(s) Assigned
13 Apr 2021Review(s) Completed, Editorial Evaluation Pending
14 Apr 2021Editorial Decision: Revise Major
26 May 20211st Revision Received
26 May 2021Submission Checks Completed
26 May 2021Assigned to Editor
26 May 2021Reviewer(s) Assigned
11 Jun 2021Review(s) Completed, Editorial Evaluation Pending