Literature DB >> 28650038

Asymmetric radical alkylation of N-sulfinimines under visible light photocatalytic conditions.

Alberto F Garrido-Castro1, Houcine Choubane, Mortada Daaou, M Carmen Maestro, José Alemán.   

Abstract

In this communication, a new photocatalytic strategy for the addition of alkyl-radical derivatives to N-sulfinimines with complete diastereoselectivity and moderate to good yields is presented. This is the first asymmetric photocatalytic addition to N-sulfinimines under visible light irradiation with smooth conditions and functional group tolerance.

Entities:  

Year:  2017        PMID： 28650038     DOI： 10.1039/c7cc03724d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  11 in total

1.  A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.

Authors:  Shengyang Ni; Alberto F Garrido-Castro; Rohan R Merchant; Justine N de Gruyter; Daniel C Schmitt; James J Mousseau; Gary M Gallego; Shouliang Yang; Michael R Collins; Jennifer X Qiao; Kap-Sun Yeung; David R Langley; Michael A Poss; Paul M Scola; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-15       Impact factor: 15.336

2.  Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors:  Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-11-29       Impact factor: 15.419

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

Authors:  Kristen M Baker; Amanda Tallon; Richard P Loach; Olivia P Bercher; Matthew A Perry; Mary P Watson
Journal:  Org Lett       Date:  2021-09-27       Impact factor: 6.072

4.  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

5.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors:  Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

6.  Diastereocontrol in Radical Addition to β-Benzyloxy Hydrazones: Revised Approach to Tubuvaline and Synthesis of O-Benzyltubulysin V Benzyl Ester.

Authors:  Manshu Li; Koushik Banerjee; Gregory K Friestad
Journal:  J Org Chem       Date:  2021-10-12       Impact factor: 4.354

7.  α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.

Authors:  Shengzu Duan; Yujin Zi; Lingling Wang; Jielun Cong; Wen Chen; Minyan Li; Hongbin Zhang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2022-03-03       Impact factor: 9.825

8.  A Visible Light-Driven Minisci-Type Reaction with N-Hydroxyphthalimide Esters.

Authors:  Lisa Marie Kammer; Aliyaah Rahman; Till Opatz
Journal:  Molecules       Date:  2018-03-27       Impact factor: 4.411

9.  Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors:  Stefano Crespi; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2020-08-06       Impact factor: 60.622

10.  Hydroxylamine-Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron-Catalyzed Preparation of Unprotected Sulfinamides from Thiols.

Authors:  Sayanti Chatterjee; Szabolcs Makai; Bill Morandi
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-10       Impact factor: 16.823
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