Literature DB >> 24074152

Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tert-alkyl N-phthalimidoyl oxalates.

Gregory L Lackner1, Kyle W Quasdorf, Larry E Overman.   

Abstract

A convenient method for the direct construction of quaternary carbons from tertiary alcohols by visible-light photoredox coupling of tert-alkyl N-phthalimidoyl oxalate intermediates with electron-deficient alkenes is reported.

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Year:  2013        PMID： 24074152      PMCID： PMC3856227          DOI： 10.1021/ja408971t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

1.  Deoxygenative functionalization of hydroxy groups via xanthates with tetraphenyldisilane

Authors: 
Journal:  J Org Chem       Date:  2000-05-09       Impact factor: 4.354

2.  Shining light on photoredox catalysis: theory and synthetic applications.

Authors:  Joseph W Tucker; Corey R J Stephenson
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

3.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

Review 4.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

5.  Factors affecting the rates of addition of free radicals to alkenes-determination of absolute rate coefficients using the persistent aminoxyl method.

Authors:  Athelstan L J Beckwith; James S Poole
Journal:  J Am Chem Soc       Date:  2002-08-14       Impact factor: 15.419

6.  A concise synthesis of (-)-aplyviolene facilitated by a strategic tertiary radical conjugate addition.

Authors:  Martin J Schnermann; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-24       Impact factor: 15.336
  6 in total
  44 in total

1.  A three-component coupling approach to the ACE-ring substructure of C19-diterpene alkaloids.

Authors:  Kosuke Minagawa; Daisuke Urabe; Masayuki Inoue
Journal:  J Antibiot (Tokyo)       Date:  2017-06-14       Impact factor: 2.649

2.  Forging C(sp3)-C(sp3) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Authors:  Spencer P Pitre; Nicholas A Weires; Larry E Overman
Journal:  J Am Chem Soc       Date:  2019-01-04       Impact factor: 15.419

3.  A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

Authors:  Tian Qin; Josep Cornella; Chao Li; Lara R Malins; Jacob T Edwards; Shuhei Kawamura; Brad D Maxwell; Martin D Eastgate; Phil S Baran
Journal:  Science       Date:  2016-04-21       Impact factor: 47.728

4.  Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated From tert-Alkyl N-Phthalimidoyl Oxalates By Visible-Light Photocatalysis.

Authors:  Gregory L Lackner; Kyle W Quasdorf; Gerald Pratsch; Larry E Overman
Journal:  J Org Chem       Date:  2015-06-01       Impact factor: 4.354

5.  Constructing Quaternary Carbons from N-(Acyloxy)phthalimide Precursors of Tertiary Radicals Using Visible-Light Photocatalysis.

Authors:  Gerald Pratsch; Gregory L Lackner; Larry E Overman
Journal:  J Org Chem       Date:  2015-06-01       Impact factor: 4.354

6.  Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis.

Authors:  Gerald Pratsch; Larry E Overman
Journal:  J Org Chem       Date:  2015-10-30       Impact factor: 4.354

7.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

8.  Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

Authors:  Christopher C Nawrat; Christopher R Jamison; Yuriy Slutskyy; David W C MacMillan; Larry E Overman
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

9.  A Concise Approach to Paxilline Indole Diterpenes.

Authors:  David T George; Eric J Kuenstner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2015-12-07       Impact factor: 15.419

10.  Diastereoselective Coupling of Chiral Acetonide Trisubstituted Radicals with Alkenes.

Authors:  Daniel J Tao; Mikko Muuronen; Yuriy Slutskyy; Alexander Le; Filipp Furche; Larry E Overman
Journal:  Chemistry       Date:  2016-05-30       Impact factor: 5.236
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