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

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概要

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• 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.

• 公益社団法人日本薬学会の論文
• 1997-05-15

著者

• Kakehi Akikazu

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Ban M

  Central Research Laboratory Kissei Pharmaceutical Co. Ltd.

• Ito Suketaka

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• KITAZAWA MAKIO

  Central Research Laboratories, KISSEI Pharmaceutical Co. Ltd

• BAN Masaaki

  Central Research Laboratory, Kissei Pharmaceutical Co., Ltd.,

• OKAZAKI Kosuke

  Central Research Laboratory, Kissei Pharmaceutical Co., Ltd.,

• OZAWA Motoyasu

  Central Research Laboratory, Kissei Pharmaceutical Co., Ltd.,

• Kitazawa M

  Central Research Laboratory Kissei Pharmaceutical Co. Ltd.

• Kitazawa Makio

  Central Research Laboratories Kissei Pharmaceutical Co. Ltd.

• Ozawa Motoyasu

  Central Research Laboratory Kissei Pharmaceutical Co. Ltd.

• Okazaki K

  Central Research Laboratory Kissei Pharmaceutical Co. Ltd.

• Ito Suketaka

  Department of Applied Chemistry Faculty of Engineering Nagoya University

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