Literature DB >> 34570516

α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines.

Kristen M Baker1, Amanda Tallon1, Richard P Loach2, Olivia P Bercher1, Matthew A Perry2, Mary P Watson1.   

Abstract

A deaminative reaction of Katritzky alkylpyridinium salts and sulfinimines has been developed to deliver enantiopure α-chiral amines. The success of this method relied on the discovery of a thermally promoted deamination via single-electron transfer of an anion-π complex of the alkylpyridinium cation with potassium carbonate. This method boasts excellent diastereoselectivity over the α-stereocenter as well as broad functional group and heterocycle tolerance.

Entities:  

Year:  2021        PMID： 34570516      PMCID： PMC8653508          DOI： 10.1021/acs.orglett.1c02708

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.072


  39 in total

Review 1.  Synthesis and applications of tert-butanesulfinamide.

Authors:  MaryAnn T Robak; Melissa A Herbage; Jonathan A Ellman
Journal:  Chem Rev       Date:  2010-06-09       Impact factor: 60.622

2.  Deaminative (Carbonylative) Alkyl-Heck-type Reactions Enabled by Photocatalytic C-N Bond Activation.

Authors:  Xuan Jiang; Mao-Mao Zhang; Wei Xiong; Liang-Qiu Lu; Wen-Jing Xiao
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-21       Impact factor: 15.336

3.  A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

4.  Anion-π Interactions in Light-Induced Reactions: Role in the Amidation of (Hetero)aromatic Systems with Activated N-Aryloxyamides.

Authors:  Laura Buglioni; Marco M Mastandrea; Antonio Frontera; Miquel A Pericàs
Journal:  Chemistry       Date:  2019-08-08       Impact factor: 5.236

5.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

6.  Deaminative Reductive Arylation Enabled by Nickel/Photoredox Dual Catalysis.

Authors:  Jun Yi; Shorouk O Badir; Lisa Marie Kammer; María Ribagorda; Gary A Molander
Journal:  Org Lett       Date:  2019-04-17       Impact factor: 6.005

7.  Synthesis of amino-diamondoid pharmacophores via photocatalytic C-H aminoalkylation.

Authors:  William K Weigel; Hoang T Dang; Hai-Bin Yang; David B C Martin
Journal:  Chem Commun (Camb)       Date:  2020-08-20       Impact factor: 6.222

8.  Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling.

Authors:  Patricia Zhang; Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-06-22       Impact factor: 15.419

9.  Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors:  Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336
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  1 in total

Review 1.  Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

Authors:  Yuan Gao; Songwei Jiang; Nian-Dong Mao; Huan Xiang; Ji-Long Duan; Xiang-Yang Ye; Li-Wei Wang; Yang Ye; Tian Xie
Journal:  Top Curr Chem (Cham)       Date:  2022-05-19
  1 in total

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