New entry of coupling reaction of phenacylamine derivatives with silylstannane.
The new coupling reaction of phenacylamines with silylstannane and lithium diisopropylamide (LDA) is reported. The treatment of a phenacylamine iodide 1 with (trimethylsilyl)tributylstannane (Me3SiSnBu3) and cesium fluoride (CsF) gave a dimerization product 2 having no iodine atom. Reaction of 1 with LDA afforded a dimerization product 3 with an iodine atom. The products 2 and 3 were separated to the meso and racemic isomers, respectively.
Iwai
Yasumasa
Y
Graduate School of Pharmaceutical Sciences, The University of Tokushima, Japan.
Kita
Kumiko
K
Matsushita
Yoko
Y
Yamauchi
Aiko
A
Kihara
Masaru
M
D000098:Acetophenones / Q000737:chemistry*; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry*; D011437:Propylamines / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D014001:Tin / Q000737:chemistry*
D000098:Acetophenones; D009942:Organometallic Compounds; D011437:Propylamines; D012821:Silanes; C024324:phenacylamine; D014001:Tin; C007442:diisopropylamine