Literature DB >> 31573212

Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides.

Andrew Whyte1, Alexa Torelli1, Bijan Mirabi1, Mark Lautens1.   

Abstract

An enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after polycyclic indolines. Futhermore, this report highlights the capability to harness reactive catalytic intermediates to exploit otherwise unreactive functional groups.

Entities:  

Year:  2019        PMID: 31573212     DOI: 10.1021/acs.orglett.9b03144

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile.

Authors:  Pedro De Jesús Cruz; Evan T Crawford; Shubin Liu; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2021-09-27       Impact factor: 16.383

Review 2.  Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors:  Weichao Xue; Martin Oestreich
Journal:  ACS Cent Sci       Date:  2020-07-09       Impact factor: 14.553

3.  Enantioselective Cu(I)-catalyzed borylative cyclization of enone-tethered cyclohexadienones and mechanistic insights.

Authors:  Sandip B Jadhav; Soumya Ranjan Dash; Sundaram Maurya; Jagadeesh Babu Nanubolu; Kumar Vanka; Rambabu Chegondi
Journal:  Nat Commun       Date:  2022-02-14       Impact factor: 17.694

4.  Synthesis of dihydroisoquinolinone-4-methylboronic esters via domino Heck/borylation using a structurally characterized palladacycle as a catalyst.

Authors:  Jhansi Rani Morla; Dastagiri Reddy Nareddula
Journal:  RSC Adv       Date:  2022-02-28       Impact factor: 3.361

5.  Enantio- and diastereoselective conjugate borylation/Mannich cyclization.

Authors:  Egor M Larin; Joachim Loup; Iuliia Polishchuk; Rachel J Ross; Andrew Whyte; Mark Lautens
Journal:  Chem Sci       Date:  2020-05-18       Impact factor: 9.825

  5 in total

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