Literature DB >> 15957896

Chiral Brønsted acid catalyzed enantioselective hydrophosphonylation of imines: asymmetric synthesis of alpha-amino phosphonates.

Takahiko Akiyama1, Hisashi Morita, Junji Itoh, Kohei Fuchibe.   

Abstract

[reaction: see text] A cyclic phosphoric acid derivative, derived from (R)-BINOL, was used as a chiral Brønsted acid (10 mol %) in hydrophosphonylation of aldimines with diisopropyl phosphite at room temperature. Alpha-amino phosphonates were obtained with good to high enantioselectivities.

Entities:  

Year:  2005        PMID： 15957896     DOI： 10.1021/ol050695e

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  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

2.  Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition.

Authors:  Michael J Smith; Kyle D Reichl; Randolph A Escobar; Thomas J Heavey; David F Coker; Scott E Schaus; John A Porco
Journal:  J Am Chem Soc       Date:  2018-12-26       Impact factor: 15.419

3.  Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines.

Authors:  Ryan R Walvoord; Marisa C Kozlowski
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  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

5.  A chiral N-phosphinyl phosphoramide: another offspring for the sage phosphoric acid progenitor.

Authors:  Jeffrey N Johnston
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-15       Impact factor: 15.336

6.  Exploration of the interrupted Fischer indolization reaction.

Authors:  Alex W Schammel; Ben W Boal; Liansuo Zu; Tehetena Mesganaw; Neil K Garg
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

7.  Enantioselective synthesis of alpha-aminopropargylphosphonates.

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

8.  Asymmetric Synthesis of β-Substituted α-Methylenebutyro- lactones via TRIP-Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)-(-)-Hydroxymatairesinol.

Authors:  Michael Fuchs; Markus Schober; Andreas Orthaber; Kurt Faber
Journal:  Adv Synth Catal       Date:  2013-08-29       Impact factor: 5.837

9.  The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction.

Authors:  Erika Bálint; Ádám Tajti; Anna Ádám; István Csontos; Konstantin Karaghiosoff; Mátyás Czugler; Péter Ábrányi-Balogh; György Keglevich
Journal:  Beilstein J Org Chem       Date:  2017-01-12       Impact factor: 2.883

10.  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
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