Literature DB >> 26558319

Diastereoselective Synthesis of α-Quaternary Aziridine-2-carboxylates via Aza-Corey-Chaykovsky Aziridination of N-tert-Butanesulfinyl Ketimino Esters.

Maurice A Marsini1, Jonathan T Reeves1, Jean-Nicolas Desrosiers1, Melissa A Herbage1, Jolaine Savoie1, Zhibin Li1, Keith R Fandrick1, C Avery Sader1, Bryan McKibben1, Donghong A Gao1, Jianwen Cui1, Nina C Gonnella1, Heewon Lee1, Xudong Wei1, Frank Roschangar1, Bruce Z Lu1, Chris H Senanayake1.   

Abstract

A general, scalable, and highly diastereoselective aziridination of N-tert-butanesulfinyl ketimino esters is described. The methodology has been utilized to provide straightforward access to previously unobtainable, biologically relevant α-quaternary amino esters and derivatives starting from readily available precursors.

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Year:  2015        PMID: 26558319     DOI: 10.1021/acs.orglett.5b02838

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


  4 in total

1.  Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-23       Impact factor: 15.336

2.  Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles.

Authors:  Jing-Wen Kang; Xiang Li; Fei-Yu Chen; Yuan Luo; Shu-Cang Zhang; Bin Kang; Cheng Peng; Xu Tian; Bo Han
Journal:  RSC Adv       Date:  2019-04-17       Impact factor: 4.036

3.  Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines.

Authors:  Sonal Bhandari; Sravani Sana; Vandana Lahoti; Ramya Tokala; Nagula Shankaraiah
Journal:  RSC Adv       Date:  2020-04-24       Impact factor: 4.036

4.  Direct Stereodivergent Olefination of Carbonyl Compounds with Sulfur Ylides.

Authors:  Jérémy Merad; Phillip S Grant; Tobias Stopka; Juliette Sabbatani; Ricardo Meyrelles; Alexander Preinfalk; Ján Matyasovsky; Boris Maryasin; Leticia González; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2022-06-30       Impact factor: 16.383

  4 in total

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