Literature DB >> 17217302

Amine-promoted, organocatalytic aziridination of enones.

Alan Armstrong1, Carl A Baxter, Scott G Lamont, Andrew R Pape, Richard Wincewicz.   

Abstract

A novel method is presented using N-N ylides (prepared by in situ amination of a tertiary amine) for the aziridination of a range of enone systems. The amine may be used sub-stoichiometrically, and promising levels of enantioselectivity are observed with quinine as promoter. [reaction: see text].

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Year:  2007        PMID： 17217302     DOI： 10.1021/ol062852v

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


  7 in total

Review 1.  Chalcone: A Privileged Structure in Medicinal Chemistry.

Authors:  Chunlin Zhuang; Wen Zhang; Chunquan Sheng; Wannian Zhang; Chengguo Xing; Zhenyuan Miao
Journal:  Chem Rev       Date:  2017-05-10       Impact factor: 60.622

2.  Simple strategy for synthesis of optically active allylic alcohols and amines by using enantioselective organocatalysis.

Authors:  Hao Jiang; Nicole Holub; Karl Anker Jørgensen
Journal:  Proc Natl Acad Sci U S A       Date:  2010-06-14       Impact factor: 11.205

3.  Regio- and Stereospecific Synthesis of Oridonin D-Ring Aziridinated Analogues for the Treatment of Triple-Negative Breast Cancer via Mediated Irreversible Covalent Warheads.

Authors:  Ye Ding; Dengfeng Li; Chunyong Ding; Pingyuan Wang; Zhiqing Liu; Eric A Wold; Na Ye; Haiying Chen; Mark A White; Qiang Shen; Jia Zhou
Journal:  J Med Chem       Date:  2018-03-20       Impact factor: 7.446

4.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

5.  A practical method for the aziridination of α,β-unsaturated carbonyl compounds with a simple carbamate utilizing sodium hypochlorite pentahydrate.

Authors:  Takehiro Umeda; Satoshi Minakata
Journal:  RSC Adv       Date:  2021-06-22       Impact factor: 3.361

Review 6.  The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines.

Authors:  Valentina C M Gasser; Szabolcs Makai; Bill Morandi
Journal:  Chem Commun (Camb)       Date:  2022-09-08       Impact factor: 6.065

7.  Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines.

Authors:  Alan Armstrong; Alexandra Ferguson
Journal:  Beilstein J Org Chem       Date:  2012-10-12       Impact factor: 2.883
  7 in total

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