Literature DB >> 22968967

Asymmetric hydrogenation of α,β-unsaturated carboxylic esters with chiral iridium N,P ligand complexes.

David H Woodmansee1, Marc-André Müller, Lars Tröndlin, Esther Hörmann, Andreas Pfaltz.   

Abstract

Enantioselective conjugate reduction of a wide range of α,β-unsaturated carboxylic esters was achieved using chiral Ir N,n>an class="Chemical">P complexes as hydrogenation catalysts. Depending on the substitution pattern of the substrate, different ligands perform best. α,β-Unsaturated carboxylic esters substituted at the α position are less problematic substrates than originally anticipated and in some cases α-substituted substrates actually reacted with higher enantioselectivity than their β-substituted analogues. The resulting saturated esters with a stereogenic center in the α or β position were obtained in high enantiomeric purity.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID: 22968967     DOI: 10.1002/chem.201202397

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  6 in total

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Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

2.  Comparison Of Asymmetric Hydrogenations Of Unsaturated- Carboxylic Acids And -Esters.

Authors:  Sakunchai Khumsubdee; Kevin Burgess
Journal:  ACS Catal       Date:  2013-02-01       Impact factor: 13.084

3.  Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones.

Authors:  Afrooz Zirakzadeh; Manuela A Groß; Yaping Wang; Kurt Mereiter; Walter Weissensteiner
Journal:  Organometallics       Date:  2014-04-09       Impact factor: 3.876

4.  Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids.

Authors:  Shuang Yang; Wen Che; Hui-Ling Wu; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2016-11-15       Impact factor: 9.825

Review 5.  The Implications of the Brønsted Acidic Properties of Crabtree-Type Catalysts in the Asymmetric Hydrogenation of Olefins.

Authors:  Bram B C Peters; Pher G Andersson
Journal:  J Am Chem Soc       Date:  2022-08-31       Impact factor: 16.383

6.  Chiral auxiliary recycling in continuous flow: automated recovery and reuse of Oppolzer's sultam.

Authors:  R J Sullivan; S G Newman
Journal:  Chem Sci       Date:  2018-01-25       Impact factor: 9.825

  6 in total

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