Literature DB >> 22616790

Effect of chiral diene ligands in rhodium-catalyzed asymmetric addition of arylboronic acids to α,β-unsaturated sulfonyl compounds.

Takahiro Nishimura1, Yuka Takiguchi, Tamio Hayashi.   

Abstract

Asymmetric addition of arylboronic acids to α,β-unsaturated sulfonyl compounds proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of the addition products with high enantioselectivity (96->99.5% ee). The diene ligand was proved to be essential for the formation of the addition products, while the use of a bisphosphine ligand mainly gave the cine-substitution product.

Entities:  

Year:  2012        PMID: 22616790     DOI: 10.1021/ja303109q

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


  5 in total

1.  Palladium(ii)-catalyzed γ-selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids.

Authors:  Rei Matsuura; Tanner C Jankins; David E Hill; Kin S Yang; Gary M Gallego; Shouliang Yang; Mingying He; Fen Wang; Rohan P Marsters; Indrawan McAlpine; Keary M Engle
Journal:  Chem Sci       Date:  2018-09-06       Impact factor: 9.825

2.  Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides.

Authors:  Balakrishna Moku; Wan-Yin Fang; Jing Leng; Linxian Li; Gao-Feng Zha; K P Rakesh; Hua-Li Qin
Journal:  iScience       Date:  2019-10-30

3.  Crown Ether-Derived Chiral BINOL: Enantioselective Michael Addition of Alkenyl Boronic Acids to α,β-Unsaturated Ketones.

Authors:  Jia-Ju Tao; Jia-Dong Tang; Tao Hong; Jia-Wen Ye; Jia-Yu Chen; Chunsong Xie; Zibin Zhang; Shijun Li
Journal:  ACS Omega       Date:  2021-12-10

4.  The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions.

Authors:  Takahiro Sawano; Pengfei Ji; Alexandra R McIsaac; Zekai Lin; Carter W Abney; Wenbin Lin
Journal:  Chem Sci       Date:  2015-09-14       Impact factor: 9.825

5.  A mild light-induced cleavage of the S-O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes.

Authors:  Maxim Ratushnyy; Monika Kamenova; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2018-07-25       Impact factor: 9.825

  5 in total

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