Literature DB >> 27813276

Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles.

Xuan Zhou1,2, Guangbin Dong1,2.   

Abstract

Herein an intramolecular nickel-catalyzed (4+2) coupling between cyclobutanones and allenes, by C-C cleavage, is reported. The reaction provides a distinct approach for accessing [3.2.2] bicyclic scaffolds which are challenging to prepare through conventional approaches. The reaction is efficient, chemoselective, and pH/redox neutral. Room temperature conditions and low catalyst loadings can be adopted. Excellent enantioselectivity is also achieved.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C activation; allenes; cycloaddition; nickel; small ring systems

Mesh：

Substances：

Year:  2016        PMID： 27813276      PMCID： PMC5161747          DOI： 10.1002/anie.201609489

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


  32 in total

1.  Cyclometalated phosphine-based pincer complexes: mechanistic insight in catalysis, coordination, and bond activation.

Authors:  Milko E van der Boom; David Milstein
Journal:  Chem Rev       Date:  2003-05       Impact factor: 60.622

2.  Phosphoramidites: privileged ligands in asymmetric catalysis.

Authors:  Johannes F Teichert; Ben L Feringa
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-29       Impact factor: 15.336

3.  Phosphine-catalyzed [4 + 2] annulation: synthesis of cyclohexenes.

Authors:  Yang S Tran; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-10-03       Impact factor: 15.419

4.  Selective 1:2 coupling of aldehydes and allenes with control of regiochemistry.

Authors:  Takeharu Toyoshima; Tomoya Miura; Masahiro Murakami
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-14       Impact factor: 15.336

5.  Highly enantioselective Rh-catalyzed carboacylation of olefins: efficient syntheses of chiral poly-fused rings.

Authors:  Tao Xu; Haye Min Ko; Nikolas A Savage; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2012-11-28       Impact factor: 15.419

6.  [4+2] and [4+3] catalytic cycloadditions of allenes.

Authors:  Fernando López; José L Mascareñas
Journal:  Chem Soc Rev       Date:  2014-03-18       Impact factor: 54.564

7.  Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones.

Authors:  Masahiro Murakami; Shinji Ashida; Takanori Matsuda
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

8.  Highly enantioselective rhodium(I)-catalyzed carbonyl carboacylations initiated by C-C bond activation.

Authors:  Laetitia Souillart; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-14       Impact factor: 15.336

9.  Cyclobutanes in catalysis.

Authors:  Tobias Seiser; Tanguy Saget; Duc N Tran; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

10.  A single step approach to piperidines via Ni-catalyzed β-carbon elimination.

Authors:  Puneet Kumar; Janis Louie
Journal:  Org Lett       Date:  2012-04-02       Impact factor: 6.005
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  6 in total

1.  Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled Electron Transfer.

Authors:  Kuo Zhao; Kenji Yamashita; Joseph E Carpenter; Trevor C Sherwood; William R Ewing; Peter T W Cheng; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2019-05-23       Impact factor: 15.419

2.  Distal-Bond-Selective C-C Activation of Ring-Fused Cyclopentanones: An Efficient Access to Spiroindanones.

Authors:  Ying Xia; Jianbo Wang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-23       Impact factor: 15.336

3.  Catalytic Enantioselective Synthesis of γ-Lactams with β-Quaternary Centers via Merging of C-C Activation and Sulfonyl Radical Migration.

Authors:  Xuan Yu; Zining Zhang; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2022-05-17       Impact factor: 16.383

Review 4.  Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity.

Authors:  Jan Sietmann; Johannes M Wahl
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-19       Impact factor: 16.823

5.  Enantioselective palladium/copper-catalyzed C-C σ-bond activation synergized with Sonogashira-type C(sp3)-C(sp) cross-coupling alkynylation.

Authors:  Feng-Na Sun; Wan-Chun Yang; Xiao-Bing Chen; Yu-Li Sun; Jian Cao; Zheng Xu; Li-Wen Xu
Journal:  Chem Sci       Date:  2019-06-21       Impact factor: 9.825

6.  Nickel-Catalyzed Asymmetric Domino Ring Opening/Cross-Coupling Reaction of Cyclobutanones via a Reductive Strategy.

Authors:  Decai Ding; Haiyan Dong; Chuan Wang
Journal:  iScience       Date:  2020-04-03
  6 in total

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