Title:
PROCESS FOR THE PREPARATION OF ORGANIC COMPOUNDS WITH IMIDE CATALYSTS
Document Type and Number:
WIPO Patent Application WO/2000/035835
Kind Code:
A1
Abstract:
A process of reacting (A) a compound capable of forming a stable radical which is selected from among (A1) oxygen compounds having carbon-hydrogen bonds at the position adjacent to the oxygen atom, (A2) carbonyl compounds and (A3) compounds having hydrocarbon groups bearing methyne carbon with (B) a radical-scavenging compound selected from among (B1) unsaturated compounds, (B2) compounds having hydrocarbon groups bearing methyne carbon, and so on in the presence of molecular oxygen by the use of an imide catalyst represented by general formula (1) or the like to thereby obtain an adduct of the compound (B) with the compound (A), a product of substitution of the compound (B) with the compound (A), or oxides of both. In said formula, R?1¿ and R?2¿ are each hydrogen or the like, or alternatively R?1¿ and R?2¿ may be united to form a double bond or an aromatic or nonaromatic ring; and X is oxygen or hydroxyl. This process makes it possible to efficiently produce various organic compounds under mild conditions through addition or substitution by the use of molecular oxygen.
Inventors:
ISHII YASUTAKA (JP)
IWAHAMA TAKAHIRO (JP)
NAKANO TATSUYA (JP)
IWAHAMA TAKAHIRO (JP)
NAKANO TATSUYA (JP)
Application Number:
PCT/JP1999/006891
Publication Date:
June 22, 2000
Filing Date:
December 09, 1999
Export Citation:
Assignee:
DAICEL CHEM (JP)
ISHII YASUTAKA (JP)
IWAHAMA TAKAHIRO (JP)
NAKANO TATSUYA (JP)
ISHII YASUTAKA (JP)
IWAHAMA TAKAHIRO (JP)
NAKANO TATSUYA (JP)
International Classes:
B01J31/02; C07C2/76; C07C29/36; C07C45/33; C07C45/34; C07C45/39; C07C49/323; C07C49/345; C07C67/347; C07D307/33; C07D315/00; C07D317/30; C08F20/30; (IPC1-7): C07B37/02; C07B37/04; C07B41/00; C07C2/82; C07C13/615; C07C29/32; C07C31/137; C07C67/333; C07C69/675; C07C69/716; C07C69/732; C07D307/32; C07D317/30; C08F20/28; C08L33/14
Domestic Patent References:
| WO1998040337A1 | 1998-09-17 |
Foreign References:
| US5714619A | 1998-02-03 | |||
| JPH10212283A | 1998-08-11 | |||
| US4843093A | 1989-06-27 | |||
| JPH10307396A | 1998-11-17 | |||
| JPH0990637A | 1997-04-04 |
Other References:
GROCHOWSKI E. ET AL.: "Reaction of diethyl azodicarboxylate with ethers in the presence of N-hydroxyimides as catalysts", SYNTHESIS,, no. 10, 1977, pages 718 - 720, XP002923606
ROUDIER J.F. & FOUCAUD A.: "Clay-catalyzed ene reactions. Synthesis of gamma-lactones", TETRAHEDRON LETTERS,, vol. 25, no. 39, 1984, pages 4375 - 4378, XP002923607
FRONZA G. ET AL.: "Stereochemistry of the microbial reduction of ketolactones", BIOTECHNOLOGY LETTERS,, vol. 16, no. 10, 1994, pages 1047 - 1052, XP002923608
MUNOZ A.H. ET AL.: "Preparation of alpha-hydroxy.gamma-lactones and their application in the synthesis of alpha, beta-butenolides; alpha-alkylidene-gamma-lactones and furans", JOURNAL OF CHEMICAL RESEARCH (SYNOP),, no. 2, 1993, pages 68 - 69, XP002923609
FRONZA G. ET AL.: "Enzyme-assisted synthesis of (S)-sotolon", TETRAHEDRON LETTERS,, vol. 33, no. 38, 1992, pages 5625 - 5628, XP002923610
SEEBACH D & WASMUTH D.: "Preparation of erythro-2-hydroxy-succinic acid derivatives from malic esters", HELVETICA CHIMICA ACTA,, vol. 63, no. 1, 1980, pages 197 - 200, XP002923611
BRENNA E. ET AL.: "On a baker's yeast-mediated approach to verapamil's optically active intermediates", TETRAHEDRON,, vol. 53, no. 30, 1997, pages 10555 - 10564, XP002923612
FOGLIATO G. ET AL.: "Baker's yeast-mediated synthesis of (R)-aminoglutethimide", THE JOURNAL OF ORGANIC CHEMISTRY,, vol. 60, no. 17, 1995, pages 5693 - 5695, XP002923613
FRONZA G. ET AL.: "Baker's yeast mediated preparation of esters of (R)- and (S)-ethyl 2-formyl-3-hydroxy-2-methyl-propionate", THE JOURNAL OF ORGANIC CHEMISTRY,, vol. 59, no. 12, 1994, pages 3487 - 3489, XP002923614
See also references of EP 1055654A4
ROUDIER J.F. & FOUCAUD A.: "Clay-catalyzed ene reactions. Synthesis of gamma-lactones", TETRAHEDRON LETTERS,, vol. 25, no. 39, 1984, pages 4375 - 4378, XP002923607
FRONZA G. ET AL.: "Stereochemistry of the microbial reduction of ketolactones", BIOTECHNOLOGY LETTERS,, vol. 16, no. 10, 1994, pages 1047 - 1052, XP002923608
MUNOZ A.H. ET AL.: "Preparation of alpha-hydroxy.gamma-lactones and their application in the synthesis of alpha, beta-butenolides; alpha-alkylidene-gamma-lactones and furans", JOURNAL OF CHEMICAL RESEARCH (SYNOP),, no. 2, 1993, pages 68 - 69, XP002923609
FRONZA G. ET AL.: "Enzyme-assisted synthesis of (S)-sotolon", TETRAHEDRON LETTERS,, vol. 33, no. 38, 1992, pages 5625 - 5628, XP002923610
SEEBACH D & WASMUTH D.: "Preparation of erythro-2-hydroxy-succinic acid derivatives from malic esters", HELVETICA CHIMICA ACTA,, vol. 63, no. 1, 1980, pages 197 - 200, XP002923611
BRENNA E. ET AL.: "On a baker's yeast-mediated approach to verapamil's optically active intermediates", TETRAHEDRON,, vol. 53, no. 30, 1997, pages 10555 - 10564, XP002923612
FOGLIATO G. ET AL.: "Baker's yeast-mediated synthesis of (R)-aminoglutethimide", THE JOURNAL OF ORGANIC CHEMISTRY,, vol. 60, no. 17, 1995, pages 5693 - 5695, XP002923613
FRONZA G. ET AL.: "Baker's yeast mediated preparation of esters of (R)- and (S)-ethyl 2-formyl-3-hydroxy-2-methyl-propionate", THE JOURNAL OF ORGANIC CHEMISTRY,, vol. 59, no. 12, 1994, pages 3487 - 3489, XP002923614
See also references of EP 1055654A4
Attorney, Agent or Firm:
Goto, Yukihisa (Higashitenma 2-chome Kita-ku Osaka-shi Osaka, Higashitenma 2-chome Kita-ku Osaka-shi Osaka, JP)
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