Stereoselective Halogenation in Friedel-Crafts Acylation of 1-Acetylindoline with Chiral 2-(Methanesulfonyloxy)propionyl Chlorides

Autor:	Akikazu Kakehi, Suketaka Ito, Masaaki Ban, Makio Kitazawa, Kosuke Okazaki, Motoyasu Ozawa
Rok vydání:	1997
Předmět:	chemistry.chemical_classification Bicyclic molecule Halogenation General Chemistry General Medicine Medicinal chemistry Haloketone Acylation chemistry.chemical_compound Acyl chloride chemistry Bromide Drug Discovery Indoline Friedel–Crafts reaction
Zdroj:	Chemical and Pharmaceutical Bulletin. 45:765-768
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.45.765
Popis:	The Friedel-Crafts acylation of 1-acetylindoline with (S)-2- or (R)-2-(methanesulfonyloxy)propionyl chloride, and aluminum chloride in dichloromethane at room temperature did not afford the expected (S)- or (R)-1-acetyl-5-[2-(methanesulfonyloxy)propionyl]indoline, but gave optically pure (R)- or (S)-1-acetyl-5-(2-chloropropionyl)indoline, whose stereochemistry at the asymmetric carbon was inverted during the reaction. Similar reaction of 1-acetylindoline with the same chiral acylating agents in the presence of aluminum bromide gave mainly the corresponding 2-bromopropionyl derivatives, but as stereo mixtures.
Databáze:	OpenAIRE
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