Literature DB >> 22082205

Catalytic kinetic resolution of cyclic secondary amines.

Michael Binanzer1, Sheng-Ying Hsieh, Jeffrey W Bode.   

Abstract

The catalytic resolution of racemic cyclic amines has been achieved by an enantioselective amidation reaction featuring an achiral N-heterocyclic carbene catalyst and a new chiral hydroxamic acid cocatalyst working in concert. The reactions proceed at room temperature, do not generate nonvolatile byproducts, and provide enantioenriched amines by aqueous extraction.
© 2011 American Chemical Society

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Year:  2011        PMID： 22082205     DOI： 10.1021/ja209472h

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


  17 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Authors:  Daniel T Cohen; Chad C Eichman; Eric M Phillips; Emily R Zarefsky; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-14       Impact factor: 15.336

3.  Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors:  Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  ACS Catal       Date:  2012-02-29       Impact factor: 13.084

4.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

5.  Hydroxamic acids in asymmetric synthesis.

Authors:  Zhi Li; Hisashi Yamamoto
Journal:  Acc Chem Res       Date:  2012-11-16       Impact factor: 22.384

6.  Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights.

Authors:  Benedikt Wanner; Imants Kreituss; Osvaldo Gutierrez; Marisa C Kozlowski; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2015-08-26       Impact factor: 15.419

7.  Potent Synergy between Spirocyclic Pyrrolidinoindolinones and Fluconazole against Candida albicans.

Authors:  Ilandari Dewage Udara Anulal Premachandra; Kevin A Scott; Chengtian Shen; Fuqiang Wang; Shelley Lane; Haoping Liu; David L Van Vranken
Journal:  ChemMedChem       Date:  2015-08-12       Impact factor: 3.466

8.  A Selenourea-Thiourea Brønsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters.

Authors:  Yingfu Lin; William J Hirschi; Anuj Kunadia; Anirudra Paul; Ion Ghiviriga; Khalil A Abboud; Rachael W Karugu; Mathew J Vetticatt; Jennifer S Hirschi; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2020-03-11       Impact factor: 15.419

9.  Stereoelectronic basis for the kinetic resolution of N-heterocycles with chiral acylating reagents.

Authors:  Sheng-Ying Hsieh; Benedikt Wanner; Philip Wheeler; André M Beauchemin; Tomislav Rovis; Jeffrey W Bode
Journal:  Chemistry       Date:  2014-05-18       Impact factor: 5.236

10.  Concerted amidation of activated esters: reaction path and origins of selectivity in the kinetic resolution of cyclic amines via N-heterocyclic carbenes and hydroxamic acid cocatalyzed acyl transfer.

Authors:  Scott E Allen; Sheng-Ying Hsieh; Osvaldo Gutierrez; Jeffrey W Bode; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2014-08-08       Impact factor: 15.419
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