Literature DB >> 22686436

Highly enantioselective electrophilic α-bromination of enecarbamates: chiral phosphoric acid and calcium phosphate salt catalysts.

Aurélien Alix1, Claudia Lalli, Pascal Retailleau, Géraldine Masson.   

Abstract

Metal-free chiral phosphoric acids and chiral calcium phosphates both catalyze highly enantio- and diastereoselective electrophilic α-bromination of enecarbamates to provide an atom-economical synthesis of enantioenriched vicinal haloamines. Either enantiomer can be formed in good yield with excellent diastereo- and enantioselectivity simply by switching the catalyst from a phosphoric acid to its calcium salt.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22686436     DOI: 10.1021/ja304095z

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


  19 in total

1.  Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

Authors:  Souvagya Biswas; Koji Kubota; Manuel Orlandi; Mathias Turberg; Dillon H Miles; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-12       Impact factor: 15.336

2.  Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

Authors:  Cheyenne S Brindle; Charles S Yeung; Eric N Jacobsen
Journal:  Chem Sci J       Date:  2013-05-01

3.  Catalytic Aminohalogenation of Alkenes and Alkynes.

Authors:  Sherry R Chemler; Michael T Bovino
Journal:  ACS Catal       Date:  2013-06-07       Impact factor: 13.084

4.  Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

Authors:  Bardia Soltanzadeh; Arvind Jaganathan; Richard J Staples; Babak Borhan
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-25       Impact factor: 15.336

5.  Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.

Authors:  Barry M Trost; James J Cregg; Nicolas Quach
Journal:  J Am Chem Soc       Date:  2017-04-04       Impact factor: 15.419

6.  Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

Authors:  R J Van Hoveln; S C Schmid; M Tretbar; C T Buttke; J M Schomaker
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

7.  Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.

Authors:  Jun-Shan Tian; Cheng-Liang Zhu; Yun-Rong Chen; Hao Xu
Journal:  Synthesis (Stuttg)       Date:  2015-06       Impact factor: 3.157

Review 8.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

9.  Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate.

Authors:  Hongjian Wang; Yonghong Ruan; Yu-Mei Lin; Haiping Xia
Journal:  Chem Sci       Date:  2021-04-07       Impact factor: 9.825

10.  A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.

Authors:  Daniel A Strassfeld; Russell F Algera; Zachary K Wickens; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2021-06-21       Impact factor: 16.383

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.