Literature DB >> 24350760

Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides.

Vittorio Pace1, James P Rae, David J Procter.   

Abstract

The first asymmetric silylation of unsaturated lactams and amides using Cu(I)-NHC catalysts and PhMe2SiBpin has been accomplished. The method has been exploited in an expedient asymmetric synthesis of the (R)-enantiomer of the nootropic drug oxiracetam.

Entities:  

Year:  2013        PMID： 24350760     DOI： 10.1021/ol4033623

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 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

2.  Studies on asymmetric total synthesis of (-)-β-hydrastine via a chiral epoxide ring-opening cascade cyclization strategy.

Authors:  Jihui Li; Tianxiao Wu; Xinjing Song; Yang Zheng; Jiaxin Meng; Qiaohua Qin; Yongxiang Liu; Dongmei Zhao; Maosheng Cheng
Journal:  RSC Adv       Date:  2020-05-19       Impact factor: 4.036

Review 3.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

Review 4.  Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry.

Authors:  Serena Monticelli; Laura Castoldi; Irene Murgia; Raffaele Senatore; Eugenia Mazzeo; Judith Wackerlig; Ernst Urban; Thierry Langer; Vittorio Pace
Journal:  Monatsh Chem       Date:  2016-12-07       Impact factor: 1.451

Review 5.  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

6.  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

7.  Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.

Authors:  Liangliang Zhang; Martin Oestreich
Journal:  Chemistry       Date:  2019-10-22       Impact factor: 5.236

8.  Direct β-selectivity of α,β-unsaturated γ-butyrolactam for asymmetric conjugate additions in an organocatalytic manner.

Authors:  Yuan Zhong; Sihua Hong; Zhengjun Cai; Shixiong Ma; Xianxing Jiang
Journal:  RSC Adv       Date:  2018-08-14       Impact factor: 4.036

9.  Copper-Catalyzed Enantioselective Hydrosilylation of gem-Difluorocyclopropenes Leading to a Stereochemical Study of the Silylated gem-Difluorocyclopropanes.

Authors:  Keisuke Sekine; Dai Akaishi; Kakeru Konagaya; Shigekazu Ito
Journal:  Chemistry       Date:  2022-05-02       Impact factor: 5.020

10.  Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides.

Authors:  Mamen Rodríguez-Fernández; Xingchen Yan; Juan F Collados; Paul B White; Syuzanna R Harutyunyan
Journal:  J Am Chem Soc       Date:  2017-09-29       Impact factor: 15.419
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