Literature DB >> 14709071

Copper(I)-catalyzed disilylation of alkylidene malonates employing a Lewis base activation strategy.

Christopher T Clark1, Jason F Lake, Karl A Scheidt.   

Abstract

The disilylation of activated alpha,alpha-unsaturated esters has been accomplished by utilizing symmetrical disilanes and catalytic quantities of copper(I) salts in the presence of Lewis bases such as DMF. This new methodology with various alkylidene malonates is moderate to high yielding and affords alpha-silyl diesters, compounds that previously have not been readily accessible, that can be further manipulated to cleanly afford useful alpha-substituted alpha-hydroxy esters.

Entities:  

Year:  2004        PMID: 14709071     DOI: 10.1021/ja038530t

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


  7 in total

1.  Enantioselective conjugate silyl additions to cyclic and acyclic unsaturated carbonyls catalyzed by Cu complexes of chiral N-heterocyclic carbenes.

Authors:  Kang-Sang Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

2.  Metal-free catalytic C-Si bond formation in an aqueous medium. Enantioselective NHC-catalyzed silyl conjugate additions to cyclic and acyclic α,β-unsaturated carbonyls.

Authors:  Jeannette M O'Brien; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

3.  Activation of Si-Si Bonds for Copper(I)-Catalyzed Conjugate Silylation.

Authors:  Laura Iannazzo; Gary A Molander
Journal:  European J Org Chem       Date:  2012-09

4.  N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.

Authors:  Troy E Reynolds; Charlotte A Stern; Karl A Scheidt
Journal:  Org Lett       Date:  2007-06-01       Impact factor: 6.005

5.  Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si.

Authors:  Hiroto Yoshida
Journal:  Chem Rec       Date:  2016-01-20       Impact factor: 6.771

Review 6.  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

7.  Sodium silylsilanolate as a precursor of silylcopper species.

Authors:  Hiroki Yamagishi; Kenshiro Hitoshio; Jun Shimokawa; Hideki Yorimitsu
Journal:  Chem Sci       Date:  2022-03-21       Impact factor: 9.825

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.