Synthesis of chiral sulfinyl-substituted 1-indolyl enones and asymmetric conjugate addition by an arylcopper reagent.
The asymmetric conjugate addition of arylcopper reagents to chiral 1-[2-(p-tolylsulfinyl)]indolyl and 1-[3-(p-tolylsulfinyl)]indolyl enones was examined. With the 2-sulfinyl-indolyl derivatives, the reaction of the arylcopper reagent gave high diastereoselectivities (81-88% de's) to afford the adducts in excellent yields, although the similar addition reaction of the 3-sulfinyl derivatives afforded poor diastereoselectivities.
Arai
Yoshitsugu
Y
Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan. arai-y@gifu-pu.ac.jp
Kasai
Makoto
M
Masaki
Yukio
Y
D003300:Copper / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis*
D007211:Indoles; D013440:Sulfides; D003300:Copper