Literature DB >> 23647080

Enantioselective synthesis of α-tri- and α-tetrasubstituted allylsilanes by copper-catalyzed asymmetric allylic substitution of allyl phosphates with silylboronates.

Momotaro Takeda1, Ryo Shintani, Tamio Hayashi.   

Abstract

A copper/N-heterocyclic carbene-catalyzed asymmetric allylic substitution of allyl phosphates with a silylboronate has been developed to give highly enantioenriched allylsilanes. High regioselectivity has been achieved by employing NaOH as the base, and this catalyst system is effective for both γ-mono- and disubstituted allyl phosphates.

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Year:  2013        PMID: 23647080     DOI: 10.1021/jo400888b

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors:  Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

Review 2.  Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors:  Weichao Xue; Martin Oestreich
Journal:  ACS Cent Sci       Date:  2020-07-09       Impact factor: 14.553

Review 3.  Recent advances in Cu-catalyzed C(sp3)-Si and C(sp3)-B bond formation.

Authors:  Balaram S Takale; Ruchita R Thakore; Elham Etemadi-Davan; Bruce H Lipshutz
Journal:  Beilstein J Org Chem       Date:  2020-04-15       Impact factor: 2.883

4.  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

Review 5.  Recent advances in copper-catalyzed asymmetric coupling reactions.

Authors:  Fengtao Zhou; Qian Cai
Journal:  Beilstein J Org Chem       Date:  2015-12-15       Impact factor: 2.883

  5 in total

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