Literature DB >> 23883313

A novel chiral bisphosphine-thiourea ligand for asymmetric hydrogenation of β,β-disubstituted nitroalkenes.

Qingyang Zhao1, Shengkun Li, Kexuan Huang, Rui Wang, Xumu Zhang.   

Abstract

A novel chiral bisphosphine-thiourea ligand was developed and applied in the highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes (up to 99% yield and 99% ee). With low catalytic loading (0.25 mol %), 98% ee and 98% conversion were obtained. The thiourea group takes on an important role in this catalytic system.

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Year:  2013        PMID： 23883313     DOI： 10.1021/ol401816y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

Review 1.  Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.

Authors:  Joost N H Reek; Bas de Bruin; Sonja Pullen; Tiddo J Mooibroek; Alexander M Kluwer; Xavier Caumes
Journal:  Chem Rev       Date:  2022-05-20       Impact factor: 72.087

2.  Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

Authors:  Qingyang Zhao; Jialin Wen; Renchang Tan; Kexuan Huang; Pedro Metola; Rui Wang; Eric V Anslyn; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-18       Impact factor: 15.336

3.  Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position.

Authors:  Xiuxiu Li; Cai You; Yusheng Yang; Yuhong Yang; Pan Li; Guoxian Gu; Lung Wa Chung; Hui Lv; Xumu Zhang
Journal:  Chem Sci       Date:  2018-01-04       Impact factor: 9.825

4.  Enantioselective [1,2]-Stevens rearrangement of thiosulfonates to construct dithio-substituted quaternary carbon centers.

Authors:  Linfeng Hu; Jinzhao Li; Yongyan Zhang; Xiaoming Feng; Xiaohua Liu
Journal:  Chem Sci       Date:  2022-03-11       Impact factor: 9.825

5.  Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines.

Authors:  Woo-Ok Jung; Binh Khanh Mai; Brian J Spinello; Zachary J Dubey; Seung Wook Kim; Craig E Stivala; Jason R Zbieg; Peng Liu; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-06-21       Impact factor: 16.383

6.  1-(2-Bromo-4-chloro-phen-yl)-3,3-di-methyl-thio-urea.

Authors:  Gamal A El-Hiti; Keith Smith; Amany S Hegazy; Mohammad Hayal Alotaibi; Benson M Kariuki
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-05-24

7.  Strong Brønsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh-thiourea chiral phosphine complex via anion binding.

Authors:  Jialin Wen; Renchang Tan; Shaodong Liu; Qingyang Zhao; Xumu Zhang
Journal:  Chem Sci       Date:  2016-01-26       Impact factor: 9.825

8.  Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst.

Authors:  Zhengyu Han; Gang Liu; Rui Wang; Xiu-Qin Dong; Xumu Zhang
Journal:  Chem Sci       Date:  2019-03-19       Impact factor: 9.825

Review 9.  Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

Authors:  Franz Steppeler; Dominika Iwan; Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Molecules       Date:  2020-01-18       Impact factor: 4.411

10.  A domino reaction for generating β-aryl aldehydes from alkynes by substrate recognition catalysis.

Authors:  Weiwei Fang; Felix Bauer; Yaxi Dong; Bernhard Breit
Journal:  Nat Commun       Date:  2019-10-25       Impact factor: 14.919
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