Literature DB >> 35975680

Catalytic Asymmetric Allylic Alkylation with Arylfluoroacetonitriles.

Archita Sripada1, Christian Wolf1.   

Abstract

A palladium(phosphinoxazoline) catalyzed method for asymmetric allylic alkylation of α-aryl-α-fluoroacetonitriles is introduced. This reaction achieves C-C bond formation and incorporation of two adjacent chirality centers with moderate to good yields, high enantioselectivities, and up to 15:1 dr.

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Year:  2022        PMID： 35975680      PMCID： PMC9444989          DOI： 10.1021/acs.joc.2c01414

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.198


  20 in total

1.  Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.

Authors:  Max Moskowitz; Kaluvu Balaraman; Christian Wolf
Journal:  J Org Chem       Date:  2018-01-22       Impact factor: 4.354

2.  Sequence-Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones.

Authors:  Xi-Jia Liu; Shicheng Jin; Wen-Yun Zhang; Qiang-Qiang Liu; Chao Zheng; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-17       Impact factor: 15.336

3.  Asymmetric synthesis of quaternary α-fluoro-β-keto-amines via detrifluoroacetylative Mannich reactions.

Authors:  Chen Xie; Yanling Dai; Haibo Mei; Jianlin Han; Vadim A Soloshonok; Yi Pan
Journal:  Chem Commun (Camb)       Date:  2015-06-04       Impact factor: 6.222

4.  Catalytic Asymmetric Mannich Reaction of α-Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters.

Authors:  Ransheng Ding; Zeus A De Los Santos; Christian Wolf
Journal:  ACS Catal       Date:  2019-02-06       Impact factor: 13.084

5.  Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-27       Impact factor: 15.336

6.  Enantioseparation and racemization of α-aryl-α-fluoroacetonitriles.

Authors:  Sarah E Steber; Angelette N D L Pham; Eryn Nelson; Christian Wolf
Journal:  Chirality       Date:  2021-10-01       Impact factor: 2.437

Review 7.  Cyanoalkylation: Alkylnitriles in Catalytic C-C Bond-Forming Reactions.

Authors:  Rosa López; Claudio Palomo
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-21       Impact factor: 15.336

8.  Stereoselective Synthesis of 3,3'-Bisindolines by Organocatalytic Michael Additions of Fluorooxindole Enolates to Isatylidene Malononitriles in Aqueous Solution.

Authors:  Kaluvu Balaraman; Ransheng Ding; Christian Wolf
Journal:  Adv Synth Catal       Date:  2017-09-22       Impact factor: 5.837

9.  Direct Catalytic Asymmetric Mannich-Type Reaction of α- and β-Fluorinated Amides.

Authors:  Lennart Brewitz; Fernando Arteaga Arteaga; Liang Yin; Kaliyamoorthy Alagiri; Naoya Kumagai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2015-12-10       Impact factor: 15.419

10.  Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Aldehydes.

Authors:  Pandur Venkatesan Balaji; Zhao Li; Akira Saito; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Chemistry       Date:  2020-11-12       Impact factor: 5.236
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