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Title:
CHIRAL CATALYSTS FOR ASYMMETRIC ACYLATION AND RELATED TRANSFORMATIONS
Document Type and Number:
WIPO Patent Application WO2001039884
Kind Code:
A3
Abstract:
A chiral catalyst comprising a 3,4-disubstituted pyridine, or a salt, N functionalised derivative, dimer or oligomer thereof, wherein the 3-substituent is substantially hindered from rotation about the bond (sp<2>-sp<2> biaryl axis) linking it to pyridine and the 4-substituent is an aliphatic or aromatic amine linked by a single bond to the pyridine, the pyridine nitrogen being functionalised or unfunctionalised, preferably comprising a compound of formula (I), wherein Z is a group substantially hindered from rotation about its bond; and each of R<1> and R<2> are independently selected from C1-30 alkyl, C3-30 cyclo alkyl and/or C3-30 aryl, or NR<1> R<2> form a cyclic amine; wherein R<1> and/or R<2> may be optionally substituted and/or include one or more heteroatoms; a composition or support comprising the catalyst; a process for the preparation and resolution thereof; and a process for stereoselective reaction of an optically inactive substrate using the catalyst. A process for the preparation of a compound of formula (I), (II) or (III) comprises cross-coupling a compound of formula (IV) with an organometal derivative R<3>-M (Scheme B).

Inventors:
SPIVEY ALAN CHRISTOPHER (GB)
FEKNER TOMASZ (US)
Application Number:
GB0004564W
Publication Date:
June 13, 2002
Filing Date:
November 30, 2000
Export Citation:
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Assignee:
UNIVERSITY OF SHEFFIELD
SPIVEY, ALAN, CHRISTOPHER
FEKNER, TOMASZ
International Classes:
B01J31/02; C07B53/00; C07B57/00; C07C67/08; C07D213/74; (IPC1-7): B01J31/02; C07D213/74; C07B37/04; C07B53/00; C07B57/00
Domestic Patent References:
WO1998022484A11998-05-28
WO2000050401A12000-08-31
Foreign References:
EP0889049A11999-01-07
Other References:
SPIVEY, ALAN C. ET AL: "Axially Chiral Analogues of 4-(Dimethylamino)pyridine: Novel Catalysts for Nonenzymatic Enantioselective Acylations" J. ORG. CHEM. (2000), 65(10), 3154-3159, XP000985947 cited in the application
SPIVEY, ALAN C. ET AL: "Configurationally Stable Biaryl Analogues of 4- (Dimethylamino)pyridine: A Novel Class of Chiral Nucleophilic Catalysts" J. ORG. CHEM. (1999), 64(26), 9430-9443, XP000985965
SPIVEY A C ET AL: "Synthesis of Atropisomeric Analogues of DMAP" TETRAHEDRON LETTERS,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 39, no. 48, 26 November 1998 (1998-11-26), pages 8919-8922, XP004140965 ISSN: 0040-4039 cited in the application
KAWABATA, T.; NAGATO, M.; TAKASU, K.; FUJI, K.: "Nonenzymatic Kinetic Resolution of Racemic Alcohols through an "Induced Fit" Process" JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 119, no. 13, 2 April 1997 (1997-04-02), pages 3169-3170, XP002165380 cited in the application
CAMPOS, PEDRO J. ET AL: "A versatile synthesis of pyrrolo-, furo- and thienopyridines via photocyclization of 3-amino-2-alkene imines in an acid medium" TETRAHEDRON (1999), 55(49), 14079-14088, XP004184726
BARLUENGA, JOSE ET AL: "Synthesis of pentasubstituted pyridines. Cycloadditions of N-vinylic heterocumulenes with 1-(N,N-diethylamine)prop-1-yne" TETRAHEDRON (1997), 53(12), 4521-4530, XP004105513
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; GRUSECK, URSULA ET AL: "The remarkable reactivity of 2-alkylideneimidazolidines in inverse Diels-Alder reactions" retrieved from STN Database accession no. 109:110325 XP002165381 & TETRAHEDRON LETT. (1987), 28(48), 6027-30,
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; BADYAR, AHMET E. ET AL: "The chemistry of 6-dialkylamino-2H-1,3-oxazin-2-ones. Reversible thermal ring-opening and cycloaddition reactions with N-arylmaleimides and 1-diethylaminopropyne. X-ray crystal structures of a 5H-2-pyridone and a 1H-2-pyridone" retrieved from STN Database accession no. 96:103373 XP002165382 & J. CHEM. SOC., PERKIN TRANS. 1 (1981), (11), 2878-83,
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; CAPUANO, LILLY ET AL: "New syntheses with diazo diketones. IV. Cyclic S-oxides" retrieved from STN Database accession no. 91:5209 XP002165383 & CHEM. BER. (1979), 112(3), 1012-22,
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SONVEAUX, ETIENNE ET AL: "[4 + 2] Cycloadditions of a vinylketenimine. New route toward functionalized cyclohexenone derivatives" retrieved from STN Database accession no. 79:91704 XP002165384 & J. AMER. CHEM. SOC. (1973), 95(16), 5417-19,
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HIRAI, KOICHI ET AL: "Reaction of CSI (chlorosulfonyl isocyanate) with a hetero-substituted carbon-carbon triple bond" retrieved from STN Database accession no. 78:159569 XP002165385 & SANKYO KENKYUSHO NEMPO (1972), 24, 108-15,
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; COSSEY, A. L. ET AL: "Amide-acid chloride adducts in organic synthesis. 3. Synthesis of pentasubstituted pyridines from C-alkyl-N,N-dialkylcyanoacetamides" retrieved from STN Database accession no. 78:71859 XP002165386 & ANGEW. CHEM., INT. ED. ENGL. (1972), 11(12), 1100-1,
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; GHOSEZ, LEON ET AL: "Cycloadditions of keteneimines to ynamines" retrieved from STN Database accession no. 75:20149 XP002165387 & ANGEW. CHEM., INT. ED. ENGL. (1971), 10(3), 184-5,
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