TY - JOUR
T1 - The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles
T2 - Application to the synthesis of (-)-balanol
AU - Unthank, Matthew G.
AU - Hussain, Nigel
AU - Aggarwal, Varinder K.
PY - 2006/10/27
Y1 - 2006/10/27
N2 - (Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts = toluene-p-sulfonyl, Tf = trifluoromethanesulfonyl).
AB - (Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts = toluene-p-sulfonyl, Tf = trifluoromethanesulfonyl).
KW - Annulation
KW - Asymmetric synthesis
KW - Natural products
KW - Ring opening
KW - Sulfur ylides
UR - http://www.scopus.com/inward/record.url?scp=33750630993&partnerID=8YFLogxK
U2 - 10.1002/anie.200602782
DO - 10.1002/anie.200602782
M3 - Article
AN - SCOPUS:33750630993
VL - 45
SP - 7066
EP - 7069
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 42
ER -