TY - JOUR
T1 - (2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines
AU - Fritz, Sven P.
AU - Ali, Zulfiquar
AU - Unthank, Matthew G.
AU - McGarrigle, Eoghan M.
AU - Aggarwal, Varinder K.
PY - 2012/12
Y1 - 2012/12
N2 - A versatile and simple methodis reported for the synthesis of bicyclic epoxide and aziridinefused heterocycles (up to 98% yield, up to 96: 4 er or up to 15: 1 dr), using a tandem Michael addition/ JohnsonCoreyChaykovsky 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.
AB - A versatile and simple methodis reported for the synthesis of bicyclic epoxide and aziridinefused heterocycles (up to 98% yield, up to 96: 4 er or up to 15: 1 dr), using a tandem Michael addition/ JohnsonCoreyChaykovsky 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.
KW - Cyclization reactions
KW - JohnsonCoreyChaykovsky annulations
KW - Stereoselective synthesis
KW - Sulfides
KW - Ylides
UR - http://www.scopus.com/inward/record.url?scp=84872849521&partnerID=8YFLogxK
U2 - 10.1002/hlca.201200455
DO - 10.1002/hlca.201200455
M3 - Article
AN - SCOPUS:84872849521
SN - 0018-019X
VL - 95
SP - 2384
EP - 2398
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 12
ER -