Literature DB >> 12862472

Asymmetric hydrosilylation of aryl ketones catalyzed by copper hydride complexed by nonracemic biphenyl bis-phosphine ligands.

Bruce H Lipshutz1, Kevin Noson, Will Chrisman, Asher Lower.   

Abstract

When complexed by selected ligands in either the BIPHEP or the SEGPHOS series, CuH is an extremely reactive catalyst capable of effecting asymmetric hydrosilylations of aromatic ketones at temperatures between -50 and -78 degrees C. Inexpensive silanes serve as stoichiometric sources of hydride. Substrate-to-ligand ratios exceeding 100000:1 have been documented. The level of induction is usually in the >90% ee category. The nature of the reagent has been investigated using spectroscopic and chemical means, although its composition remains unclear.

Entities:  

Year:  2003        PMID: 12862472     DOI: 10.1021/ja021391f

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


  19 in total

1.  A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-12       Impact factor: 15.336

2.  Enantioselective reduction of ketones and imines catalyzed by (CN-box)Re(V)-oxo complexes.

Authors:  Kristine A Nolin; Richard W Ahn; Yusuke Kobayashi; Joshua J Kennedy-Smith; F Dean Toste
Journal:  Chemistry       Date:  2010-08-16       Impact factor: 5.236

3.  A remarkably effective copper(II)-dipyridylphosphine catalyst system for the asymmetric hydrosilylation of ketones in air.

Authors:  Jing Wu; Jian-Xin Ji; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2005-02-22       Impact factor: 11.205

4.  ORGANIC CHEMISTRY. Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines.

Authors:  Yang Yang; Shi-Liang Shi; Dawen Niu; Peng Liu; Stephen L Buchwald
Journal:  Science       Date:  2015-07-03       Impact factor: 47.728

5.  Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.

Authors:  Xi-Jie Dai; Oliver D Engl; Thierry León; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

6.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Authors:  Steven J Malcolmson; Kangnan Li; Xinxin Shao
Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

7.  Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes.

Authors:  Sheng Feng; Hua Hao; Peng Liu; Stephen L Buchwald
Journal:  ACS Catal       Date:  2019-11-21       Impact factor: 13.084

8.  Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones.

Authors:  Yang Yang; Ian B Perry; Gang Lu; Peng Liu; Stephen L Buchwald
Journal:  Science       Date:  2016-06-09       Impact factor: 47.728

Review 9.  Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.

Authors:  Michael T Pirnot; Yi-Ming Wang; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

10.  Biferrocene-Based Diphosphine Ligands: Synthesis and Application of Walphos Analogues in Asymmetric Hydrogenations.

Authors:  Afrooz Zirakzadeh; Manuela A Groß; Yaping Wang; Kurt Mereiter; Felix Spindler; Walter Weissensteiner
Journal:  Organometallics       Date:  2013-02-11       Impact factor: 3.876

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