The use of sulfur ylides in the synthesis of substituted indoles.
[reaction: see text] This letter describes the insertion of rhodium carbenoids into thioindoles. C-10 thioindoles undergo fragmentation-coupling reactions when exposed to rhodium carbenoids. In an analogous fashion, ketoester- and malonate-substituted carbenoids have been found to insert into C-2 thioindoles. In contrast, vinylogous carbenoids were found to alkylate C-2 thioindoles at C-3.
Kennedy
A R
AR
Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA.
Taday
M H
MH
Rainier
J D
JD
D007211:Indoles / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*
D007211:Indoles; D013455:Sulfur; D012238:Rhodium