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Title:
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AZIRIDINES AND AMINES, COMPLEXES USED IN THE PROCESS, AND INTERMEDIATES THEREOF
Document Type and Number:
WIPO Patent Application WO/2006/003795
Kind Code:
A1
Abstract:
A process which comprises using a stable Ru(salen)(CO) complex represented by the general formula (I) or an enantiomer thereof as the catalyst and by which optically active aziridines and amines can be produced enantioselectively with a high turnover number (TON). In the general formula (I), Ar is a group represented by the general formula (VI) or (VII) wherein X's are each independently halogeno or haloalkyl; R1 and R2 are each independently hydrogen, C1-4 alkyl, or trialkylsilyl; and R3 is a bulky group.

Inventors:
Katsuki, Tsutomu (4-14-4, Kashiiekihigashi Higashi-ku, Fukuoka-sh, Fukuoka 12, 81300, JP)
Omura, Kazufumi (10th Apartment 212, 482-1 Nakanuma, Minamiashigara-sh, Kanagawa 23, 25001, JP)
Uchida, Tatsuya (Kurose Haitsu 206, 2-13-3 Hakozaki, Higashi-ku, Fukuoka-sh, Fukuoka 53, 81200, JP)
Irie, Ryo (Nexus Kashii 202, 4-7-1 Kashiihama, Higashi-ku, Fukuoka-sh, Fukuoka 16, 81300, JP)
Application Number:
PCT/JP2005/011059
Publication Date:
January 12, 2006
Filing Date:
June 16, 2005
Export Citation:
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Assignee:
JAPAN SCIENCE AND TECHNOLOGY AGENCY (1-8 Honcho 4-chome, Kawaguchi-shi Saitama, 12, 33200, JP)
Katsuki, Tsutomu (4-14-4, Kashiiekihigashi Higashi-ku, Fukuoka-sh, Fukuoka 12, 81300, JP)
Omura, Kazufumi (10th Apartment 212, 482-1 Nakanuma, Minamiashigara-sh, Kanagawa 23, 25001, JP)
Uchida, Tatsuya (Kurose Haitsu 206, 2-13-3 Hakozaki, Higashi-ku, Fukuoka-sh, Fukuoka 53, 81200, JP)
Irie, Ryo (Nexus Kashii 202, 4-7-1 Kashiihama, Higashi-ku, Fukuoka-sh, Fukuoka 16, 81300, JP)
International Classes:
C07B53/00; C07C251/24; C07C303/36; C07C311/16; C07C43/20; C07C47/57; C07C47/575; C07D203/02; C07D203/24; C07D203/26; C07F15/00; C07B61/00; C07M7/00; (IPC1-7): C07D203/02; C07B53/00; C07C43/20; C07C47/57; C07C47/575; C07C251/24; C07C303/36; C07C311/16; C07D203/24; C07D203/26; C07B61/00; C07F15/00; C07M7:00
Foreign References:
JP2002080415A2002-03-19
Other References:
KAWABATA H. ET AL: "Taikyusei Ruthenium Salen Satai no Gosei to Azide Kagobutsu o Nitrene Zenkutai to suru Fusai Aziridine-ka Hanno", CSJ: THE CHEMICAL SOCIETY OF JAPAN KOEN YOKOSHU, vol. 85, no. 2, 11 March 2005 (2005-03-11), pages 1091, XP002997768
OMURA K. ET AL: "Design of a robust Ru(salen) complex: aziridination with improved turnover number using N-arylsulfonyl azides as precursors", CHEMICAL COMMUNICATIONS, no. 18, 21 September 2004 (2004-09-21), pages 2060 - 2061, XP002997769
KOBAYASHI K. ET AL: "Azide Kagobutsu o Nitrene Senkutai to shite Mochiiru Olefin no Fuzai Aziridine-ka to Ichi Sentakuteki Fusei Amino-ka", SANKA HANNO TORONKAI, vol. 36, 20 October 2003 (2003-10-20), pages 50 - 52, XP002997770
HAMADA T. ET AL: "Highly Enantio selective Benzylic Hydroxylation with Concave Type of (Salen) manganese (III) Complex", TETRAHEDRON, vol. 54, 1998, pages 10017 - 10028, XP004129980
See also references of EP 1767524A4
Attorney, Agent or Firm:
Sugimura, Kosaku (7F Kazan Building, 2-4 Kasumigaseki 3-chome, Chiyoda-k, Tokyo 13, 10000, JP)
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