Literature DB >> 28722280

Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation.

Samantha E Shockley1, J Caleb Hethcox1, Brian M Stoltz1.   

Abstract

The first highly enantioselective iridium-catalyzed allylic alkylation that provides access to products bearing an allylic all-carbon quaternary stereogenic center has been developed. The reaction utilizes a masked acyl cyanide (MAC) reagent, which enables the one-pot preparation of α-quaternary carboxylic acids, esters, and amides with a high degree of enantioselectivity. The utility of these products is further explored through a series of diverse product transformations.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic alkylation; carboxylic acid derivatives; iridium; quaternary stereocenter; umpolung

Mesh:

Substances:

Year:  2017        PMID: 28722280      PMCID: PMC5674796          DOI: 10.1002/anie.201707015

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  34 in total

1.  Enantioselective Construction of Quaternary Stereocenters.

Authors:  Jens Christoffers; Alexander Mann
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

2.  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

3.  Study of Intermediates in Iridium-(Phosphoramidite,Olefin)-Catalyzed Enantioselective Allylic Substitution.

Authors:  Simon L Rössler; Simon Krautwald; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2017-03-07       Impact factor: 15.419

4.  Iridium-catalysed asymmetric allylic substitutions.

Authors:  Günter Helmchen; Axel Dahnz; Pierre Dübon; Mathias Schelwies; Robert Weihofen
Journal:  Chem Commun (Camb)       Date:  2006-12-06       Impact factor: 6.222

5.  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

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

Authors:  Wen-Bo Liu; Noriko Okamoto; Eric J Alexy; Allen Y Hong; Kristy Tran; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-04-18       Impact factor: 15.419

Review 7.  The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters.

Authors:  Elias J Corey; Angel Guzman-Perez
Journal:  Angew Chem Int Ed Engl       Date:  1998-03-02       Impact factor: 15.336

8.  Lewis base activation of grignard reagents with N-heterocyclic carbenes. Cu-free catalytic enantioselective additions to gamma-chloro-alpha,beta-unsaturated esters.

Authors:  Yunmi Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

9.  Synthesis of α-Quaternary Formimides and Aldehydes through Umpolung Asymmetric Copper Catalysis with Isocyanides.

Authors:  Kentaro Hojoh; Hirohisa Ohmiya; Masaya Sawamura
Journal:  J Am Chem Soc       Date:  2017-02-01       Impact factor: 15.419

10.  Enantioselective Synthesis of Quaternary Stereocenters via Chromium Catalysis.

Authors:  Yang Xiong; Guozhu Zhang
Journal:  Org Lett       Date:  2016-09-13       Impact factor: 6.005

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  10 in total

1.  Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis.

Authors:  Xingyu Jiang; Philip Boehm; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-17       Impact factor: 15.419

2.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

3.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

4.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419

5.  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

6.  CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.

Authors:  Sheng Feng; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-24       Impact factor: 15.419

7.  Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols.

Authors:  Aurapat Ngamnithiporn; Carina I Jette; Shoshana Bachman; Scott C Virgil; Brian M Stoltz
Journal:  Chem Sci       Date:  2018-01-24       Impact factor: 9.825

8.  Palladium-catalyzed tandem allylic substitution/cyclization and cascade hydrosilylated reduction: the influence of reaction parameters and hydrosilanes on the stereoselectivity.

Authors:  Peng-Wei Long; Jian-Xing Xu; Xing-Feng Bai; Zheng Xu; Zhan-Jiang Zheng; Ke-Fang Yang; Li Li; Li-Wen Xu
Journal:  RSC Adv       Date:  2018-06-22       Impact factor: 3.361

9.  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

10.  Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center.

Authors:  Yuan Yuan; Xue Zhang; Hui Qian; Shengming Ma
Journal:  Chem Sci       Date:  2020-07-22       Impact factor: 9.825

  10 in total

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