Literature DB >> 31072095

Streamlined Synthesis of C(sp3)-Rich N-Heterospirocycles Enabled by Visible-Light-Mediated Photocatalysis.

Nils J Flodén1, Aaron Trowbridge1, Darren Willcox1, Scarlett M Walton1,2, Yongjoon Kim1, Matthew J Gaunt1.   

Abstract

We report a general visible-light-mediated strategy that enables the construction of complex C(sp3)-rich N-heterospirocycles from feedstock aliphatic ketones and aldehydes with a broad selection of alkene-containing secondary amines. Key to the success of this approach was the utilization of a highly reducing Ir-photocatalyst and orchestration of the intrinsic reactivities of 1,4-cyclohexadiene and Hantzsch ester. This methodology provides streamlined access to complex C(sp3)-rich N-heterospirocycles displaying structural and functional features relevant to fragment-based lead identification programs.

Entities:  

Year:  2019        PMID： 31072095     DOI： 10.1021/jacs.9b03372

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


  9 in total

1.  Catalytic Arylboration of Spirocyclic Cyclobutenes: Rapid Access to Highly Substituted Spiro[3.n]alkanes.

Authors:  Amit Kumar Simlandy; Mao-Yun Lyu; M Kevin Brown
Journal:  ACS Catal       Date:  2021-10-06       Impact factor: 13.700

2.  Cobalt Catalyzed Reductive Spirocyclopropanation Reactions.

Authors:  Jacob Werth; Kristen Berger; Christopher Uyeda
Journal:  Adv Synth Catal       Date:  2019-11-06       Impact factor: 5.837

3.  Construction of NH-Unprotected Spiropyrrolidines and Spiroisoindolines by [4+1] Cyclizations of γ-Azidoboronic Acids with Cyclic N-Sulfonylhydrazones.

Authors:  Lucía López; María-Paz Cabal; Carlos Valdés
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-25       Impact factor: 16.823

4.  Oxa-spirocycles: synthesis, properties and applications.

Authors:  Kateryna Fominova; Taras Diachuk; Dmitry Granat; Taras Savchuk; Vladyslav Vilchynskyi; Oleksiy Svitlychnyi; Vladyslav Meliantsev; Igor Kovalchuk; Eduard Litskan; Vadym V Levterov; Valentyn R Badlo; Ruslan I Vaskevych; Alla I Vaskevych; Andrii V Bolbut; Volodymyr V Semeno; Rustam Iminov; Kostiantyn Shvydenko; Anastasiia S Kuznetsova; Yurii V Dmytriv; Daniil Vysochyn; Vasyl Ripenko; Andrei A Tolmachev; Olexandra Pavlova; Halyna Kuznietsova; Iryna Pishel; Petro Borysko; Pavel K Mykhailiuk
Journal:  Chem Sci       Date:  2021-07-27       Impact factor: 9.825

5.  Multicomponent Direct Assembly of N-Heterospirocycles Facilitated by Visible-Light-Driven Photocatalysis.

Authors:  Oliver M Griffiths; Steven V Ley
Journal:  J Org Chem       Date:  2022-09-14       Impact factor: 4.198

6.  Readily accessible sp3-rich cyclic hydrazine frameworks exploiting nitrogen fluxionality.

Authors:  Conor Dean; Sundaram Rajkumar; Stefan Roesner; Nessa Carson; Guy J Clarkson; Martin Wills; Matthew Jones; Michael Shipman
Journal:  Chem Sci       Date:  2020-01-02       Impact factor: 9.825

7.  A modular and divergent approach to spirocyclic pyrrolidines.

Authors:  Benjamin D A Shennan; Peter W Smith; Yusuke Ogura; Darren J Dixon
Journal:  Chem Sci       Date:  2020-08-07       Impact factor: 9.825

8.  Multicomponent double Mannich alkylamination involving C(sp2)-H and benzylic C(sp3)-H bonds.

Authors:  Zhencheng Lai; Rongkai Wu; Jiaming Li; Xing Chen; Linwei Zeng; Xi Wang; Jingjing Guo; Zujin Zhao; Hironao Sajiki; Sunliang Cui
Journal:  Nat Commun       Date:  2022-01-21       Impact factor: 14.919

9.  Photocatalytic α-Tertiary Amine Synthesis via C-H Alkylation of Unmasked Primary Amines.

Authors:  Alison S H Ryder; William B Cunningham; George Ballantyne; Tom Mules; Anna G Kinsella; Jacob Turner-Dore; Catherine M Alder; Lee J Edwards; Blandine S J McKay; Matthew N Grayson; Alexander J Cresswell
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-11       Impact factor: 16.823
  9 in total

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