(2‐Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines | Zendy

Fritz Sven P. | Zendy; Ali Zulfiquar | Zendy; Unthank Matthew G. | Zendy; McGarrigle Eoghan M. | Zendy; Aggarwal Varinder K. | Zendy

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(2‐Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines

Author(s) -

Fritz Sven P.,

Ali Zulfiquar,

Unthank Matthew G.,

McGarrigle Eoghan M.,

Aggarwal Varinder K.

Publication year - 2012

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201200455

Subject(s) - sulfonium , chemistry , annulation , bicyclic molecule , aziridine , stereoselectivity , epoxide , yield (engineering) , reagent , tandem , organic chemistry , stereochemistry , ring (chemistry) , catalysis , salt (chemistry) , materials science , metallurgy , composite material

A versatile and simple method is reported for the synthesis of bicyclic epoxide and aziridinefused heterocycles (up to 98% yield, up to 96 : 4 er or up to 15 : 1 dr), using a tandem Michael addition/ JohnsonCoreyChaykovsky annulation approach. A new chiral (2‐bromoethyl)sulfonium reagent is described, based on an easily available chiral sulfide; it promotes or enhances stereoselectivity in the reaction.

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