Literature DB >> 31081180

Synthesis of Enantioenriched Vicinal Tertiary and Quaternary Carbon Stereogenic Centers within an Acyclic Chain.

David Pierrot1, Ilan Marek1.   

Abstract

Overcoming the inherent difficulty to prepare quaternary carbon stereogenic centers, the diastereo- and enantioselective preparation of acyclic carbon backbones possessing vicinal quaternary and tertiary stereogenic centers (i.e. in a 1,2-relationship) causes distorted geometries and represents a very acute problem in organic synthesis. Several approaches are discussed in this minireview underlining the challenges illustrated by the rather limited number of approaches available to practitioners.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  diastereodivergence; quaternary stereogenic centers; stereogenic centers; tertiary stereogenic centers; vicinal positions

Year:  2019        PMID: 31081180     DOI: 10.1002/anie.201903188

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


  11 in total

1.  Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII -Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls.

Authors:  Sun Dongbang; Zican Shen; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

2.  Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.

Authors:  Tyler J Fulton; Alexander Q Cusumano; Eric J Alexy; Yun E Du; Haiming Zhang; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419

3.  Mechanistic Insights on the Selectivity of the Tandem Heck-Ring-Opening of Cyclopropyldiol Derivatives.

Authors:  Anthony Cohen; Alexander Kaushansky; Ilan Marek
Journal:  JACS Au       Date:  2022-03-05

4.  Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.

Authors:  Kaushalendra Patel; Veeranjaneyulu Lanke; Ilan Marek
Journal:  J Am Chem Soc       Date:  2022-04-12       Impact factor: 16.383

5.  Doubly stereoconvergent construction of vicinal all-carbon quaternary and tertiary stereocenters by Cu/Mg-catalyzed propargylic substitution.

Authors:  Xiang Pu; Qiu-Di Dang; Lei Yang; Xia Zhang; Dawen Niu
Journal:  Nat Commun       Date:  2022-05-04       Impact factor: 17.694

6.  Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring-Opening of 1,1-Biscyclopropyl Methanol Derivatives.

Authors:  Yogesh Siddaraju; Juliette Sabbatani; Anthony Cohen; Ilan Marek
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-20       Impact factor: 16.823

7.  Copper(I)-Catalyzed Synthesis of Unsymmetrical All-Carbon Bis-Quaternary Centers at the Opposing α-Carbons of Cyclohexanones.

Authors:  Joshua A Malone; Satish Chandra Philkhana; Jacob R Stepherson; Fatimat O Badmus; Frank R Fronczek; Rendy Kartika
Journal:  Org Lett       Date:  2022-06-29       Impact factor: 6.072

Review 8.  Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.

Authors:  Feng Zhou; Lei Zhu; Bo-Wen Pan; Yang Shi; Yun-Lin Liu; Jian Zhou
Journal:  Chem Sci       Date:  2020-07-28       Impact factor: 9.825

9.  Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of syn-sec,tert-Diols via (Z)-σ-Allylmetal Intermediates.

Authors:  Ming Xiang; Dana E Pfaffinger; Eliezer Ortiz; Gilmar A Brito; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-06-01       Impact factor: 16.383

Review 10.  Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.

Authors:  Holly E Bonfield; Damien Valette; David M Lindsay; Marc Reid
Journal:  Chemistry       Date:  2020-10-08       Impact factor: 5.236

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