Literature DB >> 21988131

Multicomponent catalytic asymmetric aziridination of aldehydes.

Anil K Gupta1, Munmun Mukherjee, William D Wulff.   

Abstract

The first multicomponent catalytic asymmetric aziridination reaction is developed to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity from aromatic and aliphatic aldehydes. This new method pushes the boundary of the aziridination reaction to substrates that failed with preformed imines.
© 2011 American Chemical Society

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Year:  2011        PMID： 21988131      PMCID： PMC3212731          DOI： 10.1021/ol202472z

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


  13 in total

1.  Trimethylsilyldiazomethane as a versatile stitching agent for the introduction of aziridines into functionalized organic molecules.

Authors:  Hong Ren; William D Wulff
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  Substrate-induced covalent assembly of a chemzyme and crystallographic characterization of a chemzyme-substrate complex.

Authors:  Gang Hu; Anil K Gupta; Rui H Huang; Munmun Mukherjee; William D Wulff
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

3.  Asymmetric N1 unit transfer to olefins with a chiral nitridomanganese complex: novel stereoselective pathways to aziridines or oxazolines.

Authors:  Masaaki Nishimura; Satoshi Minakata; Toru Takahashi; Yoji Oderaotoshi; Mitsuo Komatsu
Journal:  J Org Chem       Date:  2002-04-05       Impact factor: 4.354

4.  How the binding of substrates to a chiral polyborate counterion governs diastereoselection in an aziridination reaction: H-bonds in equipoise.

Authors:  Mathew J Vetticatt; Aman A Desai; William D Wulff
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

5.  Controlled diastereo- and enantioselection in a catalytic asymmetric aziridination.

Authors:  Aman A Desai; William D Wulff
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

6.  Mapping the active site in a chemzyme: diversity in the N-substituent in the catalytic asymmetric aziridination of imines.

Authors:  Yu Zhang; Zhenjie Lu; Aman Desai; William D Wulff
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005

7.  Enantioselective aza-Darzens reaction catalyzed by a chiral phosphoric acid.

Authors:  Takahiko Akiyama; Tohru Suzuki; Keiji Mori
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

8.  Evidence for a boroxinate based Brønsted acid derivative of VAPOL as the active catalyst in the catalytic asymmetric aziridination reaction.

Authors:  Gang Hu; Li Huang; Rui H Huang; William D Wulff
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

9.  Catalytic asymmetric aziridination with borate catalysts derived from VANOL and VAPOL ligands: scope and mechanistic studies.

Authors:  Yu Zhang; Aman Desai; Zhenjie Lu; Gang Hu; Zhensheng Ding; William D Wulff
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

Review 10.  Aziridine alkaloids as potential therapeutic agents.

Authors:  Fyaz M D Ismail; Dmitri O Levitsky; Valery M Dembitsky
Journal:  Eur J Med Chem       Date:  2009-05-22       Impact factor: 6.514
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  5 in total

1.  Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.

Authors:  Yong Guan; Zhensheng Ding; William D Wulff
Journal:  Chemistry       Date:  2013-10-02       Impact factor: 5.236

2.  Three-component asymmetric catalytic Ugi reaction--concinnity from diversity by substrate-mediated catalyst assembly.

Authors:  Wenjun Zhao; Li Huang; Yong Guan; William D Wulff
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-19       Impact factor: 15.336

3.  BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination.

Authors:  Anil K Gupta; Munmun Mukherjee; Gang Hu; William D Wulff
Journal:  J Org Chem       Date:  2012-09-04       Impact factor: 4.354

4.  Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines.

Authors:  Liam A McLean; Matthew W Ashford; James W B Fyfe; Alexandra M Z Slawin; Andrew G Leach; Allan J B Watson
Journal:  Chemistry       Date:  2022-02-23       Impact factor: 5.020

5.  Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.

Authors:  Xin Zhang; Richard J Staples; Arnold L Rheingold; William D Wulff
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419
  5 in total

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