Literature DB >> 19301924

Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes.

Nelmi O Devarie-Baez1, Won-Suk Kim, Amos B Smith, Ming Xian.   

Abstract

Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-tert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective bifunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp(2))-->O 1,4-Brook rearrangement. Simple organolithiums and alpha-disubstituted ester enolates prove effective as the initiating nucleophiles.

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Year:  2009        PMID： 19301924      PMCID： PMC2777545          DOI： 10.1021/ol900434k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Anion relay chemistry: an effective tactic for diversity oriented synthesis.

Authors:  Amos B Smith; Ming Xian
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

2.  The [1,5]-Brook rearrangement: an initial application in anion relay chemistry.

Authors:  Amos B Smith; Ming Xian; Won-Suk Kim; Dae-Shik Kim
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

3.  Anion relay chemistry extended. Synthesis of a gorgonian sesquiterpene.

Authors:  Amos B Smith; Dae-Shik Kim; Ming Xian
Journal:  Org Lett       Date:  2007-07-18       Impact factor: 6.005

4.  Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes.

Authors:  José Barluenga; Lorena Riesgo; Rubén Vicente; Luis A López; Miguel Tomás
Journal:  J Am Chem Soc       Date:  2008-09-19       Impact factor: 15.419

5.  An effective one-pot synthesis of 3-benzylfurans and their potential utility as versatile precursors of 3,4-dibenzyltetrahydrofuran lignans. formal synthesis of (+/-)-burseran.

Authors:  S Garçon; S Vassiliou; M Cavicchioli; B Hartmann; N Monteiro; G Balme
Journal:  J Org Chem       Date:  2001-06-01       Impact factor: 4.354

6.  Functionalized magnesium organometallics as versatile intermediates for the synthesis of polyfunctional heterocycles.

Authors:  Hiriyakkanavar Ila; Oliver Baron; Andreas J Wagner; Paul Knochel
Journal:  Chem Commun (Camb)       Date:  2005-10-05       Impact factor: 6.222

7.  A novel cyclization reaction between 2,3-bis(trimethylsilyl)buta-1,3-diene and acyl chlorides with straightforward formation of polysubstituted furans.

Authors:  Francesco Babudri; Stefania R Cicco; Gianluca M Farinola; Linda C Lopez; Francesco Naso; Vita Pinto
Journal:  Chem Commun (Camb)       Date:  2007-07-09       Impact factor: 6.222

8.  Solvent-controlled Csp2-->O silyl migration: the "one-pot" synthesis of 2,3-disubsituted thiophenes.

Authors:  Nelmi O Devarie-Baez; Brian J Shuhler; Hua Wang; Ming Xian
Journal:  Org Lett       Date:  2007-10-04       Impact factor: 6.005

Review 9.  Using singlet oxygen to synthesize polyoxygenated natural products from furans.

Authors:  Tamsyn Montagnon; Maria Tofi; Georgios Vassilikogiannakis
Journal:  Acc Chem Res       Date:  2008-07-08       Impact factor: 22.384

Review 10.  Evolution of multi-component anion relay chemistry (ARC): construction of architecturally complex natural and unnatural products.

Authors:  Amos B Smith; William M Wuest
Journal:  Chem Commun (Camb)       Date:  2008-09-30       Impact factor: 6.222
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  8 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.

Authors:  Amos B Smith; Rongbiao Tong; Won-Suk Kim; William A Maio
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-10       Impact factor: 15.336

3.  Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.

Authors:  Qi Liu; Yu Chen; Xiao Zhang; K N Houk; Yong Liang; Amos B Smith
Journal:  J Am Chem Soc       Date:  2017-06-14       Impact factor: 15.419

4.  Seebach's conjunctive reagent enables double cyclizations.

Authors:  Brent D Chandler; Jason T Roland; Yukai Li; Erik J Sorensen
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

Review 5.  Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.

Authors:  Yifan Deng; Amos B Smith
Journal:  Acc Chem Res       Date:  2020-04-09       Impact factor: 22.384

6.  (+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.

Authors:  Amos B Smith; Megan A Foley; Shuzhi Dong; Alia Orbin
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

7.  Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.

Authors:  Heeoon Han; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-10       Impact factor: 15.336

8.  Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C-Si bond functionalization.

Authors:  Sebastien Curpanen; Per Reichert; Gabriele Lupidi; Giovanni Poli; Julie Oble; Alejandro Perez-Luna
Journal:  Beilstein J Org Chem       Date:  2022-09-16       Impact factor: 2.544
  8 in total

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