Title:
光学活性含フッ素オキセタンの製造方法
Document Type and Number:
Japanese Patent JP5507285
Kind Code:
B2
Abstract:
Disclosed is a method of producing an optically active fluorinated oxetane, which can be an important pharmaceutical or agricultural intermediate, by reaction of a fluorinated ±-keto ester with an acyl alkenyl ether in the presence of a transition metal complex with an optically active ligand. This method utilizes a catalytic asymmetric synthesis process and does not require a stoichiometric amount of chiral source. It is thus possible to dramatically reduce the amount of use of the asymmetric catalyst especially when the reaction is performed at a high concentration of substrate (with the use of a small amount of reaction solvent) or in the absence of a reaction solvent (under neat conditions). Further, the target optically active fluorinated oxetane can be obtained with high yield and with very high optical purity. The product contains almost no difficult-to-separate impurity and shows high chemical purity.
Inventors:
Koichi Mikami
Kosuke Aikawa
Aida Junpei
Akio Ishii
Misato Kato
Takashi Masuda
Kosuke Aikawa
Aida Junpei
Akio Ishii
Misato Kato
Takashi Masuda
Application Number:
JP2010034169A
Publication Date:
May 28, 2014
Filing Date:
February 19, 2010
Export Citation:
Assignee:
National University Corporation Tokyo Institute of Technology
Central Glass Co., Ltd.
Central Glass Co., Ltd.
International Classes:
C07D305/08; C07B53/00; C07B61/00
Other References:
会田淳平 外,不斉ルイス酸触媒を用いた新規環化付加反応の開発,日本化学会講演予稿集,2009年 3月13日,Vol.89th, No.2,p.1029,4 F3-04
AKIYAMA,T. et al,Stereoselective construction of oxetane by titanium(IV) chloride promoted [2+2] cycloaddition of all,Chemistry Letters,1995年,No.8,p.723-724
MULLER,P. et al,Rh(II)-Catalyzed asymmetric carbene transfer with ethyl 3,3,3-trifluoro-2-diazopropionate,Tetrahedron,2004年,Vol.60, No.22,p.4755-4763
KNUNYANTS,I.L. et al.,Reactions of alkyl-trifluoropyruvates with nucleophilic reagents,Chemical Abstracts,1968年,Vol.69,p.6285,67299x
AKIYAMA,T. et al,Stereoselective construction of oxetane by titanium(IV) chloride promoted [2+2] cycloaddition of all,Chemistry Letters,1995年,No.8,p.723-724
MULLER,P. et al,Rh(II)-Catalyzed asymmetric carbene transfer with ethyl 3,3,3-trifluoro-2-diazopropionate,Tetrahedron,2004年,Vol.60, No.22,p.4755-4763
KNUNYANTS,I.L. et al.,Reactions of alkyl-trifluoropyruvates with nucleophilic reagents,Chemical Abstracts,1968年,Vol.69,p.6285,67299x
Attorney, Agent or Firm:
Makoto Koide