Literature DB >> 21848265

Enantioselective α-arylation of carbonyls via Cu(I)-bisoxazoline catalysis.

James S Harvey1, Scott P Simonovich, Christopher R Jamison, David W C MacMillan.   

Abstract

The enantioselective α-arylation of both lactones and acyl oxazolidones has been accomplished using a combination of diaryliodonium salts and copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-carbonyl benzylic stereocenters, a valuable synthon for the production of medicinal agents.

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Year:  2011        PMID： 21848265      PMCID： PMC3211083          DOI： 10.1021/ja206050b

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


  24 in total

1.  Rare-earth metal triflates in organic synthesis.

Authors:  Shū Kobayashi; Masaharu Sugiura; Hidetoshi Kitagawa; William W-L Lam
Journal:  Chem Rev       Date:  2002-06       Impact factor: 60.622

2.  Asymmetric organocatalytic alpha-arylation of aldehydes.

Authors:  José Alemán; Silvia Cabrera; Eddy Maerten; Jacob Overgaard; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Lewis base activation of Lewis acids: catalytic, enantioselective addition of silyl ketene acetals to aldehydes.

Authors:  Scott E Denmark; Gregory L Beutner; Thomas Wynn; Martin D Eastgate
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

4.  Enantioselective and diastereoselective Mukaiyama-Michael reactions catalyzed by bis(oxazoline) copper(II) complexes.

Authors:  D A Evans; K A Scheidt; J N Johnston; M C Willis
Journal:  J Am Chem Soc       Date:  2001-05-16       Impact factor: 15.419

5.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

6.  Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

Authors:  Xuebin Liao; Zhiqiang Weng; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-12-13       Impact factor: 15.419

7.  Diaryliodonium salts: a journey from obscurity to fame.

Authors:  Eleanor A Merritt; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Enantioselective alpha-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway.

Authors:  Jay C Conrad; Jongrock Kong; Brian N Laforteza; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

9.  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

10.  Palladium-catalyzed alpha-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos.

Authors:  Giang D Vo; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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  18 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents.

Authors:  Felipe Cesar Sousa E Silva; Nguyen T Van; Sarah E Wengryniuk
Journal:  J Am Chem Soc       Date:  2019-12-27       Impact factor: 15.419

3.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-05       Impact factor: 15.419

4.  Design, Synthesis, and Optimization of Balanced Dual NK1/NK3 Receptor Antagonists.

Authors:  Stephen Hanessian; Thomas Jennequin; Nicolas Boyer; Vincent Babonneau; Udaykumar Soma; Clotilde Mannoury la Cour; Mark J Millan; Guillaume De Nanteuil
Journal:  ACS Med Chem Lett       Date:  2014-02-13       Impact factor: 4.345

5.  Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

Authors:  Shaolin Zhu; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2012-06-22       Impact factor: 15.419

6.  Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: a one-step synthesis of Plavix.

Authors:  Ryan W Evans; Jason R Zbieg; Shaolin Zhu; Wei Li; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-10-16       Impact factor: 15.419

7.  The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

Authors:  Wenhan Zhang; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-27       Impact factor: 15.336

8.  Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.

Authors:  Elise Cahard; Henry P J Male; Matthieu Tissot; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419

9.  General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis.

Authors:  Lei Guo; Mingbin Yuan; Yanyan Zhang; Fang Wang; Shengqing Zhu; Osvaldo Gutierrez; Lingling Chu
Journal:  J Am Chem Soc       Date:  2020-11-19       Impact factor: 15.419

Review 10.  α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds.

Authors:  Mei Wang; Wei Wang; Dashan Li; Wen-Jing Wang; Rui Zhan; Li-Dong Shao
Journal:  Nat Prod Bioprospect       Date:  2021-06-07
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