TY - JOUR
T1 - Lewis acid-induced rearrangement of 2,3-epoxy sulfides
T2 - Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles
AU - Gill, Duncan M.
AU - Pegg, Neil A.
AU - Rayner, Christopher M.
PY - 1993/12/1
Y1 - 1993/12/1
N2 - The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.
AB - The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.
UR - http://www.scopus.com/inward/record.url?scp=37049067185&partnerID=8YFLogxK
U2 - 10.1039/P19930001371
DO - 10.1039/P19930001371
M3 - Article
AN - SCOPUS:37049067185
SP - 1371
EP - 1372
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 0300-922X
IS - 13
ER -