Literature DB >> 25219378

Chiral counteranion strategy for asymmetric oxidative C(sp³)-H/C(sp³)-H coupling: enantioselective α-allylation of aldehydes with terminal alkenes.

Pu-Sheng Wang1, Hua-Chen Lin, Yu-Jia Zhai, Zhi-Yong Han, Liu-Zhu Gong.   

Abstract

The first enantioselective α-allylation of aldehydes with terminal alkenes has been realized by combining asymmetric counteranion catalysis and palladium-catalyzed allylic C-H activation. This method can tolerate a wide scope of α-branched aromatic aldehydes and terminal alkenes, thus affording allylation products in high yields and with good to excellent levels of enantioselectivity. Importantly, the findings suggest a new strategy for the future creation of enantioselective C-H/C-H coupling reactions.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; allylic compounds; cross-coupling; enantioselectivity; palladium

Year:  2014        PMID: 25219378     DOI: 10.1002/anie.201408199

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  15 in total

1.  Synergistic palladium/enamine catalysis for asymmetric hydrocarbon functionalization of unactivated alkenes with ketones.

Authors:  Chiyu Wei; Xiaohan Ye; Qingyu Xing; Yong Hu; Yan Xie; Xiaodong Shi
Journal:  Org Biomol Chem       Date:  2019-06-25       Impact factor: 3.876

2.  Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.

Authors:  Wei Liu; Siraj Z Ali; Stephen E Ammann; M Christina White
Journal:  J Am Chem Soc       Date:  2018-08-17       Impact factor: 15.419

3.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

Review 4.  Recent applications of chiral phosphoric acids in palladium catalysis.

Authors:  Van T Tran; Sri Krishna Nimmagadda; Mingyu Liu; Keary M Engle
Journal:  Org Biomol Chem       Date:  2020-01-07       Impact factor: 3.876

5.  Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters.

Authors:  Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal:  Chem Sci       Date:  2020-01-29       Impact factor: 9.825

6.  Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Authors:  Faben A Cruz; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-11       Impact factor: 16.383

7.  Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes.

Authors:  Tuo Jiang; Teresa Bartholomeyzik; Javier Mazuela; Jochen Willersinn; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-24       Impact factor: 15.336

8.  Highly selective olefin-assisted palladium-catalyzed oxidative carbocyclization via remote olefin insertion.

Authors:  Youai Qiu; Bin Yang; Can Zhu; Jan-E Bäckvall
Journal:  Chem Sci       Date:  2016-09-15       Impact factor: 9.825

9.  Enantioselective amine α-functionalization via palladium-catalysed C-H arylation of thioamides.

Authors:  Pankaj Jain; Pritha Verma; Guoqin Xia; Jin-Quan Yu
Journal:  Nat Chem       Date:  2016-10-03       Impact factor: 24.427

10.  Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis.

Authors:  Daniel Hack; Alexander B Dürr; Kristina Deckers; Pankaj Chauhan; Nico Seling; Lukas Rübenach; Lucas Mertens; Gerhard Raabe; Franziska Schoenebeck; Dieter Enders
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-16       Impact factor: 15.336

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