Literature DB >> 25503231

Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Kyle W Quasdorf1, Larry E Overman1.   

Abstract

Quaternary carbon stereocentres-carbon atoms to which four distinct carbon substituents are attached-are common features of molecules found in nature. However, before recent advances in chemical catalysis, there were few methods of constructing single stereoisomers of this important structural motif. Here we discuss the many catalytic enantioselective reactions developed during the past decade for the synthesis of single stereoisomers of such organic molecules. This progress now makes it possible to incorporate quaternary stereocentres selectively in many organic molecules that are useful in medicine, agriculture and potentially other areas such as flavouring, fragrances and materials.

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Year:  2014        PMID: 25503231      PMCID: PMC4697831          DOI: 10.1038/nature14007

Source DB:  PubMed          Journal:  Nature        ISSN: 0028-0836            Impact factor:   49.962


  93 in total

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Journal:  J Am Chem Soc       Date:  2004-09-15       Impact factor: 15.419

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Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

3.  Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.

Authors:  David Martin; Stefan Kehrli; Magali d'Augustin; Hervé Clavier; Marc Mauduit; Alexandre Alexakis
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

4.  Rhodium-catalyzed [3 + 2] annulation of indoles.

Authors:  Yajing Lian; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

5.  Highly enantioselective proton-initiated polycyclization of polyenes.

Authors:  Karavadhi Surendra; E J Corey
Journal:  J Am Chem Soc       Date:  2012-07-10       Impact factor: 15.419

6.  Highly efficient hydrogen-bonding catalysis of the Diels-Alder reaction of 3-vinylindoles and methyleneindolinones provides carbazolespirooxindole skeletons.

Authors:  Bin Tan; Gloria Hernández-Torres; Carlos F Barbas
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

7.  Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors:  Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

8.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

9.  Total synthesis of the strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclization.

Authors:  Amy B Dounay; Philip G Humphreys; Larry E Overman; Aaron D Wrobleski
Journal:  J Am Chem Soc       Date:  2008-02-28       Impact factor: 15.419

10.  Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors:  Jiajie Feng; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-06-10       Impact factor: 15.419

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  116 in total

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Journal:  Angew Chem Int Ed Engl       Date:  2016-07-20       Impact factor: 15.336

2.  Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

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Authors:  David N Primer; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-07-18       Impact factor: 15.419

4.  Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-09       Impact factor: 15.336

5.  Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2017-07-05       Impact factor: 2.415

6.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

7.  Rhodium-Catalyzed Enantioselective Cycloisomerization to Cyclohexenes Bearing Quaternary Carbon Centers.

Authors:  Jung-Woo Park; Zhiwei Chen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419

8.  Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

9.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

10.  Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.

Authors:  Nathan R Cichowicz; Will Kaplan; Yaroslav Khomutnyk; Bijay Bhattarai; Zhankui Sun; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2015-11-10       Impact factor: 15.419

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