Literature DB >> 22954355

Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.

Wenyong Chen1, John F Hartwig.   

Abstract

We report the regio- and enantioselective allylation of an ester enolate, trimethylsiloxyfuran. This enolate reacts at the 3-position with linear aromatic allylic carbonates or aliphatic allylic benzoates to form the branched substitution products in the presence of a metallacyclic iridium catalyst. This process provides access to synthetically important 3-substituted butenolides in enantioenriched form. Stoichiometric reactions of the allyliridium intermediate suggest that the trimethylsiloxyfuran is activated by the carboxylate leaving group.

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Year:  2012        PMID： 22954355      PMCID： PMC3487469          DOI： 10.1021/ja306850b

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


  33 in total

1.  Regio- and enantioselective allylic amination of achiral allylic esters catalyzed by an iridium-phosphoramidite complex.

Authors:  Toshimichi Ohmura; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-12-25       Impact factor: 15.419

2.  Enantio- and diastereoselective ir-catalyzed allylic substitutions for asymmetric synthesis of amino acid derivatives.

Authors:  Takatoshi Kanayama; Kazumasa Yoshida; Hideto Miyabe; Yoshiji Takemoto
Journal:  Angew Chem Int Ed Engl       Date:  2003-05-09       Impact factor: 15.336

3.  Iridium-catalyzed allylic alkylation reaction with N-aryl phosphoramidite ligands: scope and mechanistic studies.

Authors:  Wen-Bo Liu; Chao Zheng; Chun-Xiang Zhuo; Li-Xin Dai; Shu-Li You
Journal:  J Am Chem Soc       Date:  2012-02-24       Impact factor: 15.419

4.  Iridium-catalyzed enantioselective synthesis of allylic alcohols: silanolates as hydroxide equivalents.

Authors:  Isabelle Lyothier; Christian Defieber; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-18       Impact factor: 15.336

5.  Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors:  John F Hartwig; Levi M Stanley
Journal:  Acc Chem Res       Date:  2010-09-28       Impact factor: 22.384

6.  Application of hitherto unexplored macrocyclization strategies in the epothilone series: novel epothilone analogs by total synthesis.

Authors:  Jon T Njardarson; Kaustav Biswas; Samuel J Danishefsky
Journal:  Chem Commun (Camb)       Date:  2002-12-07       Impact factor: 6.222

7.  Regio- and stereoselective construction of gamma-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates: an organocatalytic allylic alkylation.

Authors:  Chang-Woo Cho; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-10       Impact factor: 15.336

8.  Preparation of 2,4-disubstituted cyclopentenones by enantioselective iridium-catalyzed allylic alkylation: synthesis of 2'-methylcarbovir and TEI-9826.

Authors:  Pierre Dübon; Mathias Schelwies; Günter Helmchen
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

9.  General, regiodefined access to alpha-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory gorgonian lipid.

Authors:  John Boukouvalas; Richard P Loach
Journal:  J Org Chem       Date:  2008-09-18       Impact factor: 4.354

10.  The allyl intermediate in regioselective and enantioselective iridium-catalyzed asymmetric allylic substitution reactions.

Authors:  Sherzod T Madrahimov; Dean Markovic; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419
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  12 in total

1.  Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.

Authors:  Xingyu Jiang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

2.  Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-17       Impact factor: 15.336

3.  Construction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis.

Authors:  Wen-Bo Liu; Corey M Reeves; Scott C Virgil; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-07-12       Impact factor: 15.419

Review 4.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

5.  Cation control of diastereoselectivity in iridium-catalyzed allylic substitutions. Formation of enantioenriched tertiary alcohols and thioethers by allylation of 5H-oxazol-4-ones and 5H-thiazol-4-ones.

Authors:  Wenyong Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-12-19       Impact factor: 15.419

6.  Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion.

Authors:  Wenyong Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-01-30       Impact factor: 15.419

7.  Iridium-catalyzed enantioselective allylic substitution of unstabilized enolates derived from α,β-unsaturated ketones.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

8.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

9.  Iridium-catalyzed regio- and enantioselective allylic substitution of silyl dienolates derived from dioxinones.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-15       Impact factor: 15.336

10.  Diastereo- and enantioselective iridium-catalyzed allylation of cyclic ketone enolates: synergetic effect of ligands and barium enolates.

Authors:  Wenyong Chen; Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-10-30       Impact factor: 15.419
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