Literature DB >> 26834083

Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide.

Manabu Hatano1, Katsuya Yamakawa1, Tomoaki Kawai1, Takahiro Horibe1, Kazuaki Ishihara2,3.   

Abstract

A highly enantioselective cyanosilylation of ketones was developed by using a chiral lithium(I) phosphoryl phenoxide aqua complex as an acid/base cooperative catalyst. The pentacoordinate silicate generated in situ from Me3SiCN/LiCN acts as an extremely reactive cyano reagent. Described is a 30 gram scale reaction and the synthesis of the key precursor to (+)-13-hydroxyisocyclocelabenzine.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; homogeneous catalysis; ketones; lithium; silicates

Year:  2016        PMID: 26834083     DOI: 10.1002/anie.201510682

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


  2 in total

1.  Organocatalytic enantio- and diastereoselective cycloetherification via dynamic kinetic resolution of chiral cyanohydrins.

Authors:  Naoki Yoneda; Yuki Fujii; Akira Matsumoto; Keisuke Asano; Seijiro Matsubara
Journal:  Nat Commun       Date:  2017-11-09       Impact factor: 14.919

2.  An Entry to Enantioenriched 3,3-Disubstituted Phthalides through Asymmetric Phase-Transfer-Catalyzed γ-Alkylation.

Authors:  Marina Sicignano; Rosaria Schettini; Giovanni Pierri; Maria Leda Marino; Irene Izzo; Francesco De Riccardis; Luca Bernardi; Giorgio Della Sala
Journal:  J Org Chem       Date:  2020-05-27       Impact factor: 4.354

  2 in total

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