Literature DB >> 20806919

Rhodium-catalyzed enantioselective 1,6-addition of arylboronic acids to enynamides: asymmetric synthesis of axially chiral allenylsilanes.

Takahiro Nishimura1, Hiroki Makino, Makoto Nagaosa, Tamio Hayashi.   

Abstract

Rhodium-catalyzed asymmetric 1,6-addition of arylboronic acids to β-alkynyl acrylamides substituted with a silyl group on the alkyne terminus took place to give high yields of axially chiral allenylsilanes with 94-99% enantioselectivity, which was realized by use of a rhodium/chiral diene complex.

Entities:  

Year:  2010        PMID： 20806919     DOI： 10.1021/ja1066509

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


  11 in total

1.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

2.  Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors:  Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2019-05-15       Impact factor: 15.419

3.  Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.

Authors:  Yao Jiang; Abdallah B Diagne; Regan J Thomson; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2017-01-25       Impact factor: 15.419

4.  Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

Authors:  Thomas J O'Connor; Binh Khanh Mai; Jordan Nafie; Peng Liu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2021-08-16       Impact factor: 16.383

5.  Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors:  Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2018-02-08       Impact factor: 15.419

6.  Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes.

Authors:  Qian Yao; Yuting Liao; Lili Lin; Xiaobin Lin; Jie Ji; Xiaohua Liu; Xiaoming Feng
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

7.  Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes.

Authors:  Zheng-Li Liu; Chao Yang; Qi-Yan Xue; Meng Zhao; Cui-Cui Shan; Yun-He Xu; Teck-Peng Loh
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-04       Impact factor: 15.336

8.  Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer.

Authors:  Roly J Armstrong; Meganathan Nandakumar; Rafael M P Dias; Adam Noble; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-30       Impact factor: 15.336

9.  Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes.

Authors:  Shihua Song; Jing Zhou; Chunling Fu; Shengming Ma
Journal:  Nat Commun       Date:  2019-01-31       Impact factor: 14.919

10.  Ruthenium(ii)-catalyzed regioselective 1,6-conjugate addition of umpolung aldehydes as carbanion equivalents.

Authors:  Hyotaik Kang; Chao-Jun Li
Journal:  Chem Sci       Date:  2021-11-29       Impact factor: 9.825
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