Literature DB >> 25475991

Enantioselective synthesis of α-aminosilanes by copper-catalyzed hydroamination of vinylsilanes.

Nootaree Niljianskul1, Shaolin Zhu, Stephen L Buchwald.   

Abstract

The synthesis of α-aminosilanes by a highly enantio- and regioselective copper-catalyzed hydroamination of vinylsilanes is reported. The system employs Cu-DTBM-SEGPHOS as the catalyst, diethoxymethylsilane as the stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen source. This hydroamination reaction is compatible with differentially substituted vinylsilanes, thus providing access to amino acid mimics and other valuable chiral organosilicon compounds.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; copper; hydroamination; silicon

Mesh:

Substances:

Year:  2014        PMID: 25475991      PMCID: PMC4384418          DOI: 10.1002/anie.201410326

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


  29 in total

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Authors:  C A Chen; S M Sieburth; A Glekas; G W Hewitt; G L Trainor; S Erickson-Viitanen; S S Garber; B Cordova; S Jeffry; R M Klabe
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2.  Organosilicon molecules with medicinal applications.

Authors:  Annaliese K Franz; Sean O Wilson
Journal:  J Med Chem       Date:  2012-11-06       Impact factor: 7.446

3.  Stereospecific synthesis of cyclobutylboronates through copper(I)-catalyzed reaction of homoallylic sulfonates and a diboron derivative.

Authors:  Hajime Ito; Takashi Toyoda; Masaya Sawamura
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

4.  Silanediol inhibitors of angiotensin-converting enzyme. Synthesis and evaluation of four diastereomers of Phe[Si]Ala dipeptide analogues.

Authors:  Jaeseung Kim; Gregory Hewitt; Patrick Carroll; Scott McN Sieburth
Journal:  J Org Chem       Date:  2005-07-22       Impact factor: 4.354

5.  Activation of the Si-B linkage: copper-catalyzed addition of nucleophilic silicon to imines.

Authors:  Devendra J Vyas; Roland Fröhlich; Martin Oestreich
Journal:  Org Lett       Date:  2011-03-18       Impact factor: 6.005

6.  Efficient, enantioselective assembly of silanediol protease inhibitors.

Authors:  Yingjian Bo; Swapnil Singh; Hoan Quoc Duong; Cui Cao; Scott McN Sieburth
Journal:  Org Lett       Date:  2011-03-07       Impact factor: 6.005

7.  Iridium-catalyzed (Z)-trialkylsilylation of terminal olefins.

Authors:  Biao Lu; J R Falck
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

8.  Stereocontrolled synthesis of methyl silanediol peptide mimics.

Authors:  Lone Nielsen; Karl B Lindsay; Jesper Faber; Niels Christian Nielsen; Troels Skrydstrup
Journal:  J Org Chem       Date:  2007-11-15       Impact factor: 4.354

9.  Asymmetric synthesis of alpha-amino allyl, benzyl, and propargyl silanes by metalation and rearrangement.

Authors:  Scott McN Sieburth; Heather K O'Hare; Jiayi Xu; Yanping Chen; Guodong Liu
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

10.  Enantioselective alpha-silyl amino acid synthesis by reverse-aza-Brook rearrangement.

Authors:  Guodong Liu; Scott McN Sieburth
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005

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  26 in total

1.  A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-12       Impact factor: 15.336

Review 2.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

3.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

4.  CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.

Authors:  Haoxuan Wang; Jeffrey C Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-06-15       Impact factor: 15.419

5.  ORGANIC CHEMISTRY. Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines.

Authors:  Yang Yang; Shi-Liang Shi; Dawen Niu; Peng Liu; Stephen L Buchwald
Journal:  Science       Date:  2015-07-03       Impact factor: 47.728

6.  Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.

Authors:  Xi-Jie Dai; Oliver D Engl; Thierry León; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

7.  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

8.  An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.

Authors:  Zhishi Ye; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

9.  Copper-Catalyzed Enantioselective Hydroamination of Alkenes.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Organic Synth       Date:  2018

10.  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

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