Straightforward stereoselective synthesis of spiro-epoxyoxindoles.
[reaction: see text] The in situ preparation of a sulfonium ylide reagent achieved the highly diastereoselective epoxidation of isatins, so that a new and straightforward access to biologically significant spiro-epoxyoxindoles is provided. The first investigations of an asymmetric version are reported with enantiopure sulfides.
Schulz
Verena
V
Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ENSICAEN Université de Caen, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
Davoust
Marion
M
Lemarié
Margareth
M
Lohier
Jean-François
JF
Santos
Jana Sopkova de Oliveira
JS
Metzner
Patrick
P
Brière
Jean-François
JF
D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; C095912:N-methylisatin