Literature DB >> 15053588

Thiourea-catalyzed enantioselective hydrophosphonylation of imines: practical access to enantiomerically enriched alpha-amino phosphonic acids.

Guy D Joly1, Eric N Jacobsen.   

Abstract

Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.

Entities:  

Year:  2004        PMID： 15053588     DOI： 10.1021/ja0494398

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


  22 in total

1.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

2.  Thiourea-catalyzed enantioselective cyanosilylation of ketones.

Authors:  Douglas E Fuerst; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

3.  An Overview of Stereoselective Synthesis of α-Aminophosphonic Acids and Derivatives.

Authors:  Mario Ordóñez; Haydée Rojas-Cabrera; Carlos Cativiela
Journal:  Tetrahedron       Date:  2009-01-03       Impact factor: 2.457

4.  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

5.  Toward a practical and waste-free synthesis of thioureas in water.

Authors:  Najmedin Azizi; Alireza Khajeh-Amiri; Hossein Ghafuri; Mohammad Bolourtchian
Journal:  Mol Divers       Date:  2010-02-24       Impact factor: 2.943

6.  Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched α-amino phosphine oxides.

Authors:  Gajendrasingh K Ingle; Yuxue Liang; Michael G Mormino; Guilong Li; Frank R Fronczek; Jon C Antilla
Journal:  Org Lett       Date:  2011-03-17       Impact factor: 6.005

7.  Evaluation of ecotoxicological impact of new pyrrole-derived aminophosphonates using selected bioassay battery.

Authors:  Jarosław Lewkowski; Marta Morawska; Rafał Karpowicz; Piotr Rychter; Diana Rogacz; Kamila Lewicka; Piotr Dobrzyński
Journal:  Ecotoxicology       Date:  2017-05-30       Impact factor: 2.823

8.  Mechanism of amido-thiourea catalyzed enantioselective imine hydrocyanation: transition state stabilization via multiple non-covalent interactions.

Authors:  Stephan J Zuend; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2009-10-28       Impact factor: 15.419

9.  Enantioselective synthesis of alpha-aminopropargylphosphonates.

Authors:  Rajasekhar Dodda; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2007-06-18       Impact factor: 2.415

10.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419
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