Literature DB >> 22821705

Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles.

Jan Streuff1, Markus Feurer, Plamen Bichovski, Georg Frey, Urs Gellrich.   

Abstract

Reduction, please! The title reaction affords α-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22821705     DOI: 10.1002/anie.201204469

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  7 in total

1.  Mechanistic Studies Inform Design of Improved Ti(salen) Catalysts for Enantioselective [3 + 2] Cycloaddition.

Authors:  Sophia G Robinson; Xiangyu Wu; Binyang Jiang; Matthew S Sigman; Song Lin
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419

2.  Enantioselective cyclizations and cyclization cascades of samarium ketyl radicals.

Authors:  Nicolas Kern; Mateusz P Plesniak; Joseph J W McDouall; David J Procter
Journal:  Nat Chem       Date:  2017-08-07       Impact factor: 24.427

3.  Diastereoselective and enantioselective photoredox pinacol coupling promoted by titanium complexes with a red-absorbing organic dye.

Authors:  Francesco Calogero; Giandomenico Magagnano; Simone Potenti; Francesco Pasca; Andrea Fermi; Andrea Gualandi; Paola Ceroni; Giacomo Bergamini; Pier Giorgio Cozzi
Journal:  Chem Sci       Date:  2022-04-21       Impact factor: 9.969

4.  Recent advances in the chemistry of ketyl radicals.

Authors:  Áron Péter; Soumitra Agasti; Oliver Knowles; Emma Pye; David J Procter
Journal:  Chem Soc Rev       Date:  2021-03-23       Impact factor: 54.564

5.  Cascade radical reaction of substrates with a carbon-carbon triple bond as a radical acceptor.

Authors:  Hideto Miyabe; Ryuta Asada; Yoshiji Takemoto
Journal:  Beilstein J Org Chem       Date:  2013-06-13       Impact factor: 2.883

6.  Triazol-substituted titanocenes by strain-driven 1,3-dipolar cycloadditions.

Authors:  Andreas Gansäuer; Andreas Okkel; Lukas Schwach; Laura Wagner; Anja Selig; Aram Prokop
Journal:  Beilstein J Org Chem       Date:  2014-07-17       Impact factor: 2.883

Review 7.  New advances in titanium-mediated free radical reactions.

Authors:  Bianca Rossi; Simona Prosperini; Nadia Pastori; Angelo Clerici; Carlo Punta
Journal:  Molecules       Date:  2012-12-11       Impact factor: 4.411

  7 in total

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