Literature DB >> 26764019

Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes.

John R Coombs1, James P Morken2.   

Abstract

Terminal alkenes are readily available functional groups which appear in α-olefins produced by the chemical industry, and they appear in the products of many contemporary synthetic reactions. While the organic transformations that apply to alkenes are amongst the most studied reactions in all of chemical synthesis, the number of reactions that apply to nonactivated terminal alkenes in a catalytic enantioselective fashion is small in number. This Minireview highlights the cases where stereocontrol in catalytic reactions of 1-alkenes is high enough to be useful for asymmetric synthesis.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; asymmetric synthesis; chirality; enantioselective catalysis; transition metals

Mesh:

Substances:

Year:  2016        PMID: 26764019      PMCID: PMC4913282          DOI: 10.1002/anie.201507151

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


  84 in total

1.  Ir(I)-catalyzed intermolecular regio- and enantioselective hydroamination of alkenes with heteroaromatic amines.

Authors:  Shiguang Pan; Kohei Endo; Takanori Shibata
Journal:  Org Lett       Date:  2012-01-18       Impact factor: 6.005

2.  Asymmetric epoxidation of terminal alkenes with hydrogen peroxide catalyzed by pentafluorophenyl PtII complexes.

Authors:  Marco Colladon; Alessandro Scarso; Paolo Sgarbossa; Rino A Michelin; Giorgio Strukul
Journal:  J Am Chem Soc       Date:  2006-11-01       Impact factor: 15.419

Review 3.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
Journal:  Chem Soc Rev       Date:  2009-07-10       Impact factor: 54.564

4.  D2-symmetric dirhodium catalyst derived from a 1,2,2-triarylcyclopropanecarboxylate ligand: design, synthesis and application.

Authors:  Changming Qin; Vyacheslav Boyarskikh; Jørn H Hansen; Kenneth I Hardcastle; Djamaladdin G Musaev; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-11-02       Impact factor: 15.419

5.  Asymmetric olefin aziridination using a newly designed Ru(CO)(salen) complex as the catalyst.

Authors:  Chungsik Kim; Tatsuya Uchida; Tsutomu Katsuki
Journal:  Chem Commun (Camb)       Date:  2012-06-11       Impact factor: 6.222

6.  Iridium-catalyzed, intermolecular hydroamination of unactivated alkenes with indoles.

Authors:  Christo S Sevov; Jianrong Steve Zhou; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-02-13       Impact factor: 15.419

7.  Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation.

Authors:  Amanda D Worthy; Candice L Joe; Thomas E Lightburn; Kian L Tan
Journal:  J Am Chem Soc       Date:  2010-10-27       Impact factor: 15.419

8.  New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis.

Authors:  Arab K El-Qisairi; Hanan A Qaseer; George Katsigras; Philip Lorenzi; Unnati Trivedi; Sylvia Tracz; Amy Hartman; Jason A Miller; Patrick M Henry
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

9.  Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors:  John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

10.  The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.

Authors:  Pavel Kočovský; Jan-E Bäckvall
Journal:  Chemistry       Date:  2014-11-05       Impact factor: 5.236

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  29 in total

1.  Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors:  Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-12-22       Impact factor: 15.419

2.  Palladium-Catalyzed Dearomative syn-1,4-Oxyamination.

Authors:  Conghui Tang; Mikiko Okumura; Hejun Deng; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-20       Impact factor: 15.336

3.  Cu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with pivZPhos as the Ligand.

Authors:  Linglin Wu; Olga Zatolochnaya; Bo Qu; Ling Wu; Lucille A Wells; Marisa C Kozlowski; Chris H Senanayake; Jinhua J Song; Yongda Zhang
Journal:  Org Lett       Date:  2019-10-24       Impact factor: 6.005

4.  Catalyst Controlled Regiodivergent Arylboration of Dienes.

Authors:  Stephen R Sardini; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-07-12       Impact factor: 15.419

5.  Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors:  Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-11-29       Impact factor: 15.419

6.  Enantio- and Diastereoselective Synthesis of Hydroxy Bis(boronates) via Cu-Catalyzed Tandem Borylation/1,2-Addition.

Authors:  Jacob C Green; Matthew V Joannou; Stephanie A Murray; Joseph M Zanghi; Simon J Meek
Journal:  ACS Catal       Date:  2017-05-25       Impact factor: 13.084

7.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

Authors:  Xiaoxu Qi; Tianning Diao
Journal:  ACS Catal       Date:  2020-07-02       Impact factor: 13.084

8.  Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides.

Authors:  Joseph Derosa; Roman Kleinmans; Van T Tran; Malkanthi K Karunananda; Steven R Wisniewski; Martin D Eastgate; Keary M Engle
Journal:  J Am Chem Soc       Date:  2018-12-17       Impact factor: 15.419

9.  Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes.

Authors:  Pin Gao; Liang-An Chen; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-08-20       Impact factor: 15.419

10.  Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.

Authors:  Jiaming Li; Robert H Grubbs; Brian M Stoltz
Journal:  Org Lett       Date:  2016-10-18       Impact factor: 6.005

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