Title:
PRODUCTION OF OXY-MICHAEL ADDUCTS
Document Type and Number:
WIPO Patent Application WO2004085344
Kind Code:
A3
Abstract:
The invention provides a method of producing an oxy-Michael adduct comprising allowing a Michael acceptor to react with an alkoxide of an alcohol of formula R<1>0H having a chiral centre at the hydroxy carbon, in the presence of a multidentate ligand. The use of the multidentate ligand significantly increases stereoselectivity of the reaction. In a further aspect the multidentate ligand is not essential but the R<1> group is removed from the oxy-Michael adduct by acidic solvolysis. In a further aspect in which the multidentate ligand is not essential the alcohol R<1>0H is a lactol.
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Inventors:
DIXON DARREN (GB)
BUCHANAN DAVID (GB)
BUCHANAN DAVID (GB)
Application Number:
PCT/GB2004/001230
Publication Date:
November 11, 2004
Filing Date:
March 24, 2004
Export Citation:
Assignee:
UNIV CAMBRIDGE TECH (GB)
DIXON DARREN (GB)
BUCHANAN DAVID (GB)
DIXON DARREN (GB)
BUCHANAN DAVID (GB)
International Classes:
C07B41/04; C07B53/00; C07C67/317; C07C271/16; C07D309/10; C07D407/12; (IPC1-7): C07B41/04; C07B53/00; C07D309/10
Other References:
D. ENDERS: "Diastereo- and enantioselective synthesis of vicinal amino alcohols by oxa Michael addition of N-formylnorephedrine to nitro alkenes", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no. 9, 1 September 1998 (1998-09-01), pages 1771 - 1792, XP002295523
J. L. DUFFY: "Lithium, potassium, and sodium alkoxides: donors in the Michael addition reaction of alpha-nitroolefins", TETRAHEDRON LETTERS, vol. 34, no. 8, 19 February 1998 (1998-02-19), pages 1259 - 1260, XP000345124
N. J. ADDERLEY ET AL: "Highly diastereoselective oxy-Michael additions of enantiopure delta-lactol anions to nitroalkenes: asymmetric synthesis of 1,2-amino alcohols", ANGEWANDTE CHEMIE INT. ED., vol. 42, 15 September 2003 (2003-09-15), WEINHEIM, pages 4241 - 4244, XP002295524
D. J. BUCHANAN ET AL: "Short asymmetric syntheses of bioactve beta-aryl ethanlamine derivatives via the highly diastereoselective delta lactol oxy-Michael addition", TETRAHEDRON ASYMMETRY, vol. 15, no. 2, 26 January 2004 (2004-01-26), pages 195 - 197, XP004483482
J. L. DUFFY: "Lithium, potassium, and sodium alkoxides: donors in the Michael addition reaction of alpha-nitroolefins", TETRAHEDRON LETTERS, vol. 34, no. 8, 19 February 1998 (1998-02-19), pages 1259 - 1260, XP000345124
N. J. ADDERLEY ET AL: "Highly diastereoselective oxy-Michael additions of enantiopure delta-lactol anions to nitroalkenes: asymmetric synthesis of 1,2-amino alcohols", ANGEWANDTE CHEMIE INT. ED., vol. 42, 15 September 2003 (2003-09-15), WEINHEIM, pages 4241 - 4244, XP002295524
D. J. BUCHANAN ET AL: "Short asymmetric syntheses of bioactve beta-aryl ethanlamine derivatives via the highly diastereoselective delta lactol oxy-Michael addition", TETRAHEDRON ASYMMETRY, vol. 15, no. 2, 26 January 2004 (2004-01-26), pages 195 - 197, XP004483482
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