Literature DB >> 15876019

Samarium diiodide-catalyzed diastereoselective pinacol couplings.

Helen C Aspinall1, Nicholas Greeves, Carine Valla.   

Abstract

A complex of samarium diiodide (SmI(2)) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me(2)SiCl(2) and Mg. Diastereoselectivity of up to 95/5 (+/-/meso) has been achieved for aliphatic aldehydes and up to 19/81 (+/-/meso) for aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions using the SmI(2)/tetraglyme/Mg/Me(2)SiCl(2) catalytic system.

Entities:  

Year:  2005        PMID： 15876019     DOI： 10.1021/ol050256f

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Asymmetric Organocatalytic Reductive Coupling Reactions between Benzylidene Pyruvates and Aldehydes.

Authors:  Matthew A Horwitz; Blane P Zavesky; Jesus I Martinez-Alvarado; Jeffrey S Johnson
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

2.  Post-Assembly Reactivity of N-Aryl Iminoboronates: Reversible Radical Coupling and Unusual B-N Dynamic Covalent Chemistry.

Authors:  Evan N Keyzer; Alexandru Sava; Tanya K Ronson; Jonathan R Nitschke; Anna J McConnell
Journal:  Chemistry       Date:  2018-07-25       Impact factor: 5.236

3.  Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes.

Authors:  Matthew A Horwitz; Naoya Tanaka; Takuya Yokosaka; Daisuke Uraguchi; Jeffrey S Johnson; Takashi Ooi
Journal:  Chem Sci       Date:  2015-07-30       Impact factor: 9.825

4.  SmI2-Catalyzed Intermolecular Coupling of Cyclopropyl Ketones and Alkynes: A Link between Ketone Conformation and Reactivity.

Authors:  Soumitra Agasti; Nicholas A Beattie; Joseph J W McDouall; David J Procter
Journal:  J Am Chem Soc       Date:  2021-02-25       Impact factor: 15.419
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.