TY - JOUR
T1 - Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines
AU - Yar, Muhammad
AU - Unthank, Matthew G.
AU - McGarrigle, Eoghan M.
AU - Aggarwal, Varinder K.
PY - 2011/2/1
Y1 - 2011/2/1
N2 - The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide.
AB - The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide.
KW - azepine
KW - epoxidation
KW - medium-ring compounds
KW - nitrogen heterocycles
KW - sulfur ylide
UR - http://www.scopus.com/inward/record.url?scp=79251510869&partnerID=8YFLogxK
U2 - 10.1002/asia.201000817
DO - 10.1002/asia.201000817
M3 - Article
C2 - 21254413
AN - SCOPUS:79251510869
VL - 6
SP - 372
EP - 375
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 2
ER -