Literature DB >> 25394374

The catalytic asymmetric Abramov reaction.

Joyram Guin1, Qinggang Wang, Manuel van Gemmeren, Benjamin List.   

Abstract

The first catalytic enantioselective Abramov reaction is described. The process is based on the utilization of a chiral disulfonimide catalyst, which efficiently avoids the difficulties encountered with metal-based catalysts. Several functionalized α-hydroxy phosphonates were synthesized in good yields and with excellent enantiomeric ratios of up to >99:1. The process was shown to be scalable and up to 1 g of starting material could be employed under mild reaction conditions.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Abramov reaction; disulfonimides; hydrophosphonylations; organocatalysis; α-hydroxy phosphonates

Year:  2014        PMID: 25394374     DOI: 10.1002/anie.201409411

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

1.  Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes.

Authors:  Zhipeng Zhang; Han Yong Bae; Joyram Guin; Constantinos Rabalakos; Manuel van Gemmeren; Markus Leutzsch; Martin Klussmann; Benjamin List
Journal:  Nat Commun       Date:  2016-08-17       Impact factor: 14.919

Review 2.  Recent Developments in Organophosphorus Flame Retardants Containing P-C Bond and Their Applications.

Authors:  Sophie Wendels; Thiebault Chavez; Martin Bonnet; Khalifah A Salmeia; Sabyasachi Gaan
Journal:  Materials (Basel)       Date:  2017-07-11       Impact factor: 3.623

3.  Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates.

Authors:  Abhijnan Ray Choudhury; Santanu Mukherjee
Journal:  Chem Sci       Date:  2016-08-19       Impact factor: 9.825

4.  Continuous Flow Alcoholysis of Dialkyl H-Phosphonates with Aliphatic Alcohols.

Authors:  Erika Bálint; Ádám Tajti; Nóra Tóth; György Keglevich
Journal:  Molecules       Date:  2018-07-03       Impact factor: 4.411

5.  Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride.

Authors:  Babak Kaboudin; Sajedeh Alavi; Foad Kazemi; Hiroshi Aoyama; Tsutomu Yokomatsu
Journal:  ACS Omega       Date:  2019-09-10

6.  Efficient synthesis of ether phosphonates using trichloroacetimidate and acetate coupling methods.

Authors:  Walid Fathalla; Ibrahim A I Ali; Pavel Pazdera
Journal:  RSC Adv       Date:  2018-02-15       Impact factor: 3.361

  6 in total

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