Literature DB >> 26448575

Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters.

Zackaria Nairoukh1, Ilan Marek2.   

Abstract

The regio- and stereoselective formation of stereodefined polysubstituted silyl ketene aminals is easily achieved through selective combined carbometalation-oxidation-silylation reactions. These substrates are ideal candidates for Mukaiyama aldol reactions with aliphatic aldehydes as they give the aldol products with a quaternary carbon stereocenter α to the carbonyl groups in outstanding diastereoselectivities.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Mukaiyama reaction; aldols; one-pot reactions; quaternary carbon stereocenters; silyl ketene aminals

Year:  2015        PMID: 26448575     DOI: 10.1002/anie.201507209

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


  4 in total

1.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

2.  Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates.

Authors:  Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2018-08-02       Impact factor: 15.419

3.  Zirconocene catalyzed diastereoselective carbometalation of cyclobutenes.

Authors:  Sudipta Raha Roy; Hendrik Eijsberg; Jeffrey Bruffaerts; Ilan Marek
Journal:  Chem Sci       Date:  2016-08-30       Impact factor: 9.825

4.  Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.

Authors:  Zackaria Nairoukh; Gunda G K S Narayana Kumar; Yury Minko; Ilan Marek
Journal:  Chem Sci       Date:  2016-09-15       Impact factor: 9.825

  4 in total

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