Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines

Journal of the American Chemical Society
Xinxin ShaoSteven J Malcolmson

Abstract

Here we report highly efficient and chemoselective azadiene-imine reductive couplings catalyzed by (Ph-BPE)Cu-H that afford anti-1,2-diamines. In all cases, reactions take place with either aldimine or ketimine electrophiles to deliver a single diastereomer of product in >95:5 er. The products' diamines are easily differentiable, facilitating downstream synthesis.

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Citations

Feb 13, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marzena Wosińska-HrydczukJacek Skarżewski
Mar 25, 2021·Journal of the American Chemical Society·Sheng Feng, Stephen L Buchwald
Jun 5, 2021·Chemical Science·Shengzu DuanPatrick J Walsh
Mar 1, 2019·Journal of the American Chemical Society·Chengxi LiStephen L Buchwald
Nov 24, 2020·Organic Letters·Chenchen WangYifeng Chen
Sep 12, 2018·Organic Letters·Miao ZhanXia Zhang
Oct 18, 2019·The Journal of Organic Chemistry·Xiaofeng WangQian Chen
Nov 8, 2018·Organic Letters·Mingfeng LiFanke Meng
Nov 14, 2018·Journal of the American Chemical Society·Pei-Jun YangZhuo Chai
Jan 31, 2019·Journal of the American Chemical Society·Yuxuan YeStephen L Buchwald
Nov 6, 2020·The Journal of Organic Chemistry·Luis M Mori-QuirozMichael D Clift
Nov 20, 2019·Journal of the American Chemical Society·Zhonglin TaoScott E Denmark
Oct 12, 2018·Chemical Reviews·Shaojian TangJason J Chruma

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