Literature DB >> 27052660

Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement.

Wen-Bo Liu1, Noriko Okamoto1, Eric J Alexy1, Allen Y Hong1, Kristy Tran1, Brian M Stoltz1.   

Abstract

A catalytic, enantioselective γ-alkylation of α,β-unsaturated malonates and ketoesters is reported. This strategy entails a highly regio- and enantioselective iridium-catalyzed α-alkylation of an extended enolate, and a subsequent translocation of chirality to the γ-position via a Cope rearrangement.

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Year:  2016        PMID： 27052660      PMCID： PMC5497580          DOI： 10.1021/jacs.6b02153

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


  42 in total

1.  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

2.  Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation.

Authors:  Alexandre Alexakis; Damien Polet
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

3.  Cooperative organocatalysis for the asymmetric γ alkylation of α-branched enals.

Authors:  Giulia Bergonzini; Silvia Vera; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-10       Impact factor: 15.336

4.  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

5.  Exploration of the enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters.

Authors:  Tapas Paul; William P Malachowski; Jisun Lee
Journal:  J Org Chem       Date:  2007-02-02       Impact factor: 4.354

6.  The enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters. Application to the synthesis of (+)-mesembrine.

Authors:  Tapas Paul; William P Malachowski; Jisun Lee
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

7.  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

8.  The total synthesis of hyperpapuanone, hyperibone L, epi-clusianone and oblongifolin A.

Authors:  Nicole Biber; Katrin Möws; Bernd Plietker
Journal:  Nat Chem       Date:  2011-10-16       Impact factor: 24.427

9.  Asymmetric α,γ-Regioselective [3 + 3] Formal Cycloadditions of α,β-Unsaturated Aldehydes via Cascade Dienamine-Dienamine Catalysis.

Authors:  Wei Xiao; Xiang Yin; Zhi Zhou; Wei Du; Ying-Chun Chen
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

10.  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
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  13 in total

1.  Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements.

Authors:  Ehsan Fereyduni; Ouidad Lahtigui; Jacob N Sanders; Breanna M Tomiczek; Michael D Mannchen; Roland A Yu; K N Houk; Alexander J Grenning
Journal:  J Org Chem       Date:  2021-01-21       Impact factor: 4.354

2.  Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Authors:  Xingyu Jiang; Jason J Beiger; John F Hartwig
Journal:  J Am Chem Soc       Date:  2016-12-22       Impact factor: 15.419

3.  Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-28       Impact factor: 15.336

4.  Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Org Lett       Date:  2017-03-14       Impact factor: 6.005

5.  Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  ACS Catal       Date:  2016-08-17       Impact factor: 13.084

6.  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

7.  Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account.

Authors:  Samantha E Shockley; J Caleb Hethcox; Brian M Stoltz
Journal:  Synlett       Date:  2018-08-15       Impact factor: 2.454

8.  Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols.

Authors:  Hua Zhang; Xiao-Yu Zhan; Yu Dong; Jian Yang; Shuai He; Zhi-Chuan Shi; Xiao-Mei Zhang; Ji-Yu Wang
Journal:  RSC Adv       Date:  2020-04-30       Impact factor: 4.036

9.  Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement.

Authors:  Xi-Shang Sun; Xing-Heng Wang; Hai-Yan Tao; Liang Wei; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2020-09-17       Impact factor: 9.825

10.  Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins.

Authors:  Rahul Sarkar; Sankash Mitra; Santanu Mukherjee
Journal:  Chem Sci       Date:  2018-06-04       Impact factor: 9.825
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