Literature DB >> 20309472

The synthesis of chiral N-heterocyclic carbene-borane and -diorganoborane complexes and their use in the asymmetric reduction of ketones.

David M Lindsay1, David McArthur.   

Abstract

Chiral N-heterocyclic carbene-borane complexes have been synthesised, and have been shown to reduce ketones with Lewis acid promotion. Chiral N-heterocyclic carbene-borane and -diorganoborane complexes can reduce ketones with enantioselectivities up to 75% and 85% ee, respectively.

Entities:  

Year:  2010        PMID: 20309472     DOI: 10.1039/c001466d

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


  4 in total

1.  CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF₃ and BH₃.

Authors:  Julien Monot; Louis Fensterbank; Max Malacria; Emmanuel Lacôte; Steven J Geib; Dennis P Curran
Journal:  Beilstein J Org Chem       Date:  2010-08-02       Impact factor: 2.883

2.  Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid.

Authors:  Vladimir Lamm; Xiangcheng Pan; Tsuyoshi Taniguchi; Dennis P Curran
Journal:  Beilstein J Org Chem       Date:  2013-04-08       Impact factor: 2.883

3.  A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.

Authors:  Jeffrey M Farrell; Roy T Posaratnanathan; Douglas W Stephan
Journal:  Chem Sci       Date:  2015-01-26       Impact factor: 9.825

4.  Reductive α-borylation of α,β-unsaturated esters using NHC-BH3 activated by I2 as a metal-free route to α-boryl esters.

Authors:  James E Radcliffe; Valerio Fasano; Ralph W Adams; Peiran You; Michael J Ingleson
Journal:  Chem Sci       Date:  2018-11-19       Impact factor: 9.825

  4 in total

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