Literature DB >> 16622499

Direct synthesis of chiral aziridines from N-tert-butyl-sulfinylketimines.

Daniel Morton1, David Pearson, Robert A Field, Robert A Stockman.   

Abstract

The direct preparation of a range of variously substituted chiral tert-butylsulfinylketimines was achieved in good yield (41-90%), with relatively rapid reaction times (4-15 hours); their synthetic application was examined through the reaction with the ylides derived from trimethylsulfonium iodide and S-allyl tetrahydrothiophenium bromide, affording convenient access to a diverse range of highly substituted chiral aziridines in up to 78% yield and > 90% d.e.

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Year:  2006        PMID: 16622499     DOI: 10.1039/b601527a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  5 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.  Construct indeno[1,2-b]oxepine or cis-cyclopropylacrylate by sulfur ylides.

Authors:  Qinfang Chen; Yihao Pan; Dongxin Zhao; Weiran Yang; Jing Zheng
Journal:  RSC Adv       Date:  2020-06-08       Impact factor: 3.361

3.  K3PO4-promoted domino reactions: diastereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-tert-butanesulfinyl imines and sulfur ylides.

Authors:  Minxuan Zhang; Tianyu Lu; Yun Zhao; Guixian Xie; Zhiwei Miao
Journal:  RSC Adv       Date:  2019-04-16       Impact factor: 4.036

4.  Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; Aaron D Trowbridge; James A Bull
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

5.  Gold-Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines.

Authors:  Christian Knittl-Frank; Iakovos Saridakis; Thomas Stephens; Rafael Gomes; James Neuhaus; Antonio Misale; Rik Oost; Alberto Oppedisano; Nuno Maulide
Journal:  Chemistry       Date:  2020-06-08       Impact factor: 5.020

  5 in total

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