Literature DB >> 34668705

Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex.

Finn Burg1, Tomislav Rovis1.   

Abstract

The direct oxyamination of olefins is a compelling tool to rapidly access β-amino alcohols-a privileged motif ubiquitous in natural products, pharmaceuticals and agrochemicals. Although a variety of expedient methods are established for simple alkenes, selective amino oxygenation of 1,3-dienes is less explored. Within this context, methods for the oxyamination of 1,3-dienes that are selective for the internal position remain unprecedented. We herein report a modular three-component approach to perform an internal and highly diastereoselective amino oxygenation of 1,3-dienes catalyzed by a cationic heptamethylindenyl (Ind*) Rh(III) complex.

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Year:  2021        PMID: 34668705      PMCID: PMC8862119          DOI: 10.1021/jacs.1c09276

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  30 in total

1.  1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis.

Authors:  David J. Ager; Indra Prakash; David R. Schaad
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

2.  Intermolecular, Branch-Selective, and Redox-Neutral Cp*IrIII -Catalyzed Allylic C-H Amidation.

Authors:  Tobias Knecht; Shobhan Mondal; Jian-Heng Ye; Mowpriya Das; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-17       Impact factor: 15.336

3.  Mechanistic studies on the Rh(III)-mediated amido transfer process leading to robust C-H amination with a new type of amidating reagent.

Authors:  Yoonsu Park; Kyung Tae Park; Jeung Gon Kim; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2015-03-30       Impact factor: 15.419

4.  The Mechanism of Rhodium Catalyzed Allylic C-H Amination.

Authors:  Robert J Harris; Jiyong Park; Taylor A F Nelson; Nafees Iqbal; Daniel C Salgueiro; John Bacsa; Cora E MacBeth; Mu-Hyun Baik; Simon B Blakey
Journal:  J Am Chem Soc       Date:  2020-03-02       Impact factor: 15.419

5.  Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: efficient synthesis of morpholines and 2-morpholones.

Authors:  Ke Wen; Zhengxing Wu; Buyun Chen; Jianzhong Chen; Wanbin Zhang
Journal:  Org Biomol Chem       Date:  2018-08-08       Impact factor: 3.876

6.  Iron-catalyzed aminohydroxylation of olefins.

Authors:  Kevin S Williamson; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

7.  Rh(III)-Catalyzed Three-Component Syn-Carboamination of Alkenes Using Arylboronic Acids and Dioxazolones.

Authors:  Sumin Lee; Tomislav Rovis
Journal:  ACS Catal       Date:  2021-06-30       Impact factor: 13.700

Review 8.  Beyond osmium: progress in 1,2-amino oxygenation of alkenes, 1,3-dienes, alkynes, and allenes.

Authors:  Brett N Hemric
Journal:  Org Biomol Chem       Date:  2020-11-11       Impact factor: 3.876

9.  A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources.

Authors:  Sumin Lee; Honghui Lei; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-08-05       Impact factor: 15.419

10.  Catalytic diamination of olefins via N-N bond activation.

Authors:  Yingguang Zhu; Richard G Cornwall; Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  Acc Chem Res       Date:  2014-11-17       Impact factor: 22.384

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  1 in total

1.  Highly regioselective and diastereodivergent aminomethylative annulation of dienyl alcohols enabled by a hydrogen-bonding assisting effect.

Authors:  Yao Huang; Suchen Zou; Bangkui Yu; Xuyang Yan; Song Liu; Hanmin Huang
Journal:  Chem Sci       Date:  2022-02-02       Impact factor: 9.825

  1 in total

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