Catalytic activation of the leaving group in the S(N)2 reaction.
A novel catalytic activation of the leaving group in the S(N)2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)(2) to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives resulted in inversion of stereochemistry, which is a definitive feature of the S(N)2 reaction. The procedure is applicable for benzoazepine synthesis.
Yamamoto
Hirofumi
H
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Pandey
Ghanshyam
G
Asai
Yumiko
Y
Nakano
Mayo
M
Kinoshita
Atsushi
A
Namba
Kosuke
K
Imagawa
Hiroshi
H
Nishizawa
Mugio
M
D002384:Catalysis; D017669:Mercury Compounds / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*
D017669:Mercury Compounds; D009584:Nitrogen