Literature DB >> 24588738

An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides.

Thomas H West1, David S B Daniels, Alexandra M Z Slawin, Andrew D Smith.   

Abstract

Benzotetramisole promotes the catalytic asymmetric [2,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).

Entities:  

Mesh：

Substances：

Year:  2014        PMID： 24588738     DOI： 10.1021/ja500758n

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


  19 in total

1.  Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Authors:  Xingyu Jiang; Jason J Beiger; John F Hartwig
Journal:  J Am Chem Soc       Date:  2016-12-22       Impact factor: 15.419

2.  Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.

Authors:  Kevin J Schwarz; Colin M Pearson; Gabriel A Cintron-Rosado; Peng Liu; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-18       Impact factor: 15.336

3.  Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides.

Authors:  Bin Xu; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-17       Impact factor: 15.336

4.  Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation.

Authors:  Travis Menard; Aragorn Laverny; Scott E Denmark
Journal:  J Org Chem       Date:  2021-10-21       Impact factor: 4.354

5.  3,3-Difluoroallyl ammonium salts: highly versatile, stable and selective gem-difluoroallylation reagents.

Authors:  Fei Ye; Yao Ge; Anke Spannenberg; Helfried Neumann; Li-Wen Xu; Matthias Beller
Journal:  Nat Commun       Date:  2021-05-31       Impact factor: 14.919

6.  Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions.

Authors:  Anastassia Matviitsuk; James E Taylor; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chemistry       Date:  2016-10-11       Impact factor: 5.236

7.  Regioselectivity and Mechanism of Synthesizing N-Substituted 2-Pyridones and 2-Substituted Pyridines via Metal-Free C-O and C-N Bond-Cleaving of Oxazoline[3,2-a]pyridiniums.

Authors:  Bo Li; Susu Xue; Yang Yang; Jia Feng; Peng Liu; Yong Zhang; Jianming Zhu; Zhijian Xu; Adrian Hall; Bo Zhao; Jiye Shi; Weiliang Zhu
Journal:  Sci Rep       Date:  2017-01-25       Impact factor: 4.379

8.  Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study.

Authors:  Thomas H West; Daniel M Walden; James E Taylor; Alexander C Brueckner; Ryne C Johnston; Paul Ha-Yeon Cheong; Guy C Lloyd-Jones; Andrew D Smith
Journal:  J Am Chem Soc       Date:  2017-03-10       Impact factor: 15.419

9.  Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement.

Authors:  Stéphanie S M Spoehrle; Thomas H West; James E Taylor; Alexandra M Z Slawin; Andrew D Smith
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

10.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.