Literature DB >> 24161001

A highly efficient and enantioselective intramolecular Cannizzaro reaction under TOX/Cu(II) catalysis.

Pan Wang1, Wen-Jie Tao, Xiu-Li Sun, Saihu Liao, Yong Tang.   

Abstract

An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.

Entities:  

Year:  2013        PMID： 24161001     DOI： 10.1021/ja409859x

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


  10 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

Authors:  Nivedita S Mahajani; Rowan I L Meador; Tomas J Smith; Sarah E Canarelli; Arijit A Adhikari; Jigisha P Shah; Christopher M Russo; Daniel R Wallach; Kyle T Howard; Alexandra M Millimaci; John D Chisholm
Journal:  J Org Chem       Date:  2019-05-30       Impact factor: 4.354

3.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

4.  One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Authors:  Qiong-Jie Liu; Wen-Guang Yan; Lijia Wang; X Peter Zhang; Yong Tang
Journal:  Org Lett       Date:  2015-08-07       Impact factor: 6.005

5.  A highly efficient group-assisted purification method for the synthesis of poly-functionalized pyrimidin-5-yl-pyrroles via one-pot four-component domino reaction.

Authors:  Yuvaraj Dommaraju; Dipak Prajapati
Journal:  Mol Divers       Date:  2014-08-31       Impact factor: 2.943

6.  Enantioselective C-H Olefination of α-Hydroxy and α-Amino Phenylacetic Acids by Kinetic Resolution.

Authors:  Kai-Jiong Xiao; Ling Chu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-22       Impact factor: 15.336

7.  Biomimetic catalytic transformation of toxic α-oxoaldehydes to high-value chiral α-hydroxythioesters using artificial glyoxalase I.

Authors:  Sang Yeon Park; In-Soo Hwang; Hyun-Ju Lee; Choong Eui Song
Journal:  Nat Commun       Date:  2017-04-04       Impact factor: 14.919

8.  A Mild, Fast, and Scalable Synthesis of Substituted α-Acyloxy Ketones via Multicomponent Reaction Using a Continuous Flow Approach.

Authors:  Carlos Eduardo M Salvador; Carlos Kleber Z Andrade
Journal:  Front Chem       Date:  2019-07-30       Impact factor: 5.221

9.  One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes.

Authors:  Laurence Burroughs; Lee Eccleshare; John Ritchie; Omkar Kulkarni; Barry Lygo; Simon Woodward; William Lewis
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-29       Impact factor: 15.336

10.  Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (S)-Profens and Profenols.

Authors:  Erika Tassano; Kurt Faber; Mélanie Hall
Journal:  Adv Synth Catal       Date:  2018-06-12       Impact factor: 5.837
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.