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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.