Title:
IODOARENE DERIVATIVE, METHOD FOR PRODUCING OPTICALLY ACTIVE SPIROLACTONE COMPOUND USING SAME, AND METHOD FOR PRODUCING OPTICALLY ACTIVE CYCLIZATION ADDUCT
Document Type and Number:
WIPO Patent Application WO/2012/121248
Kind Code:
A1
Abstract:
A method for highly enantio-selectively producing an optically active spirolactone compound using a iodoarene derivative which can be easily synthesized and scarcely racemized. From 2,6-dihydroxyiodoarene, a flexibly designable hypervalent iodine compound precursor (a iodoarene derivative) is synthesized in short steps using 1,2-amino alcohol as a chiral source. Using a catalytic amount of the precursor, a hypervalent iodine compound is prepared in situ in the presence of a stoichiometric amount of m-CPBA, and 3-(1-hydroxy-2-naphthyl)propionic acid is subjected to spirolactonization. As a result, a corresponding spirolactone compound can be obtained with a high enantiomer excess.
Inventors:
ISHIHARA KAZUAKI (JP)
UYANIK MUHAMMET (JP)
YASUI TAKESHI (JP)
UYANIK MUHAMMET (JP)
YASUI TAKESHI (JP)
Application Number:
PCT/JP2012/055679
Publication Date:
September 13, 2012
Filing Date:
March 06, 2012
Export Citation:
Assignee:
UNIV NAGOYA NAT UNIV CORP (JP)
ISHIHARA KAZUAKI (JP)
UYANIK MUHAMMET (JP)
YASUI TAKESHI (JP)
ISHIHARA KAZUAKI (JP)
UYANIK MUHAMMET (JP)
YASUI TAKESHI (JP)
International Classes:
C07C217/20; C07C233/69; C07C235/48; C07C271/12; C07C311/17; C07D307/94; C07D317/72; C07B61/00
Foreign References:
| JP2010503620A | 2010-02-04 | |||
| JP2011052572A | 2011-03-17 |
Other References:
UYANIK,M. ET AL.: "Enantioselective Kita Oxidative Spirolactonization Catalyzed by In Situ Generated Chiral Hypervalent Iodine(III) Species", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 49, no. 12, 2010, pages 2175 - 2177, XP055122641
UYANIK,M. ET AL.: "Chiral hypervalent iodine- catalyzed enantioselective oxidative Kita spirolactonization of 1-naphthol derivatives and one-pot diastereo-selective oxidation to epoxyspirolactones", TETRAHEDRON, vol. 66, no. 31, 2010, pages 5841 - 5851, XP027122610
ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 49, 2010, pages 2175 - 2177
ORG. SYN., vol. 84, 2007, pages 272
See also references of EP 2684863A4
UYANIK,M. ET AL.: "Chiral hypervalent iodine- catalyzed enantioselective oxidative Kita spirolactonization of 1-naphthol derivatives and one-pot diastereo-selective oxidation to epoxyspirolactones", TETRAHEDRON, vol. 66, no. 31, 2010, pages 5841 - 5851, XP027122610
ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 49, 2010, pages 2175 - 2177
ORG. SYN., vol. 84, 2007, pages 272
See also references of EP 2684863A4
Attorney, Agent or Firm:
ITEC INTERNATIONAL PATENT FIRM (JP)
Patent business corporation Itec international patent firm (JP)
Patent business corporation Itec international patent firm (JP)
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