(E) Enol ethers from the stereoselective reduction of α-alkoxy-β-ketophosphonates and Wittig type reaction

作者: Wissam Dayoub , Alain Doutheau

DOI: 10.1007/S11426-010-4057-1

关键词:

摘要: When α-alkoxy-β-ketophosphonates, prepared by the Rh(II) mediated insertion reaction of α-diazo-β-ketophosphonates into OH bond primary alcohols, were reduced either NaBH4 in presence CaCl2 or DIBAL, they respectively gave corresponding anti syn stereomeric hydroxyphosphonates with pronounced to complete stereoselectivity. Submitted action potassium tert-butoxyde, isomers led pure (E) enol ethers moderate good yields. Under same conditions a mixture (Z) and rather poor The sequence was applied preparation some allyl-vinyl configuration for vinylic double bond.

参考文章(28)
G. Bryon Gill, The Wolff Rearrangement Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis. ,vol. 3, pp. 887- 912 ,(1991) , 10.1016/B978-0-08-052349-1.00085-8
Mark R Crimmin, Varinder K Aggarwal, Samantha L Riches, Science of Synthesis George Thieme Verlag. ,(2005)
Martin Hiersemann, Lars Abraham, Catalysis of the Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers European Journal of Organic Chemistry. ,vol. 2002, pp. 1461- 1471 ,(2002) , 10.1002/1099-0690(200205)2002:9<1461::AID-EJOC1461>3.0.CO;2-1
Florence Charbonnier, Albert Moyano, Andrew E. Greene, Facile synthesis of chiral O-alkyl enol ethers Journal of Organic Chemistry. ,vol. 52, pp. 2303- 2306 ,(1987) , 10.1021/JO00387A038
Christopher J. Moody, Eric-Robert H.B. Sie, Janusz J. Kulagowski, The use of diazophosphonates in the synthesis of cyclic ethers Tetrahedron. ,vol. 48, pp. 3991- 4004 ,(1992) , 10.1016/S0040-4020(01)88479-9
Mohamed Boukraa, Wissam Dayoub, Alain Doutheau, Highly Wolff Selective Rh(II) Catalysed Decomposition of α-Diazo- β-Ketophosphonates Having an Oxygen Atom Adjacent to the γ-Position Letters in Organic Chemistry. ,vol. 3, pp. 204- 206 ,(2006) , 10.2174/157017806775789877
Arthur F. Kluge, Ian S. Cloudsdale, Phosphonate reagents for the synthesis of enol ethers and one-carbon homologation to aldehydes Journal of Organic Chemistry. ,vol. 11, pp. 4847- 4852 ,(1979) , 10.1021/JO00394A022
Steven V. Ley, Development of methods suitable for natural product synthesis: The azadirachtin story Pure and Applied Chemistry. ,vol. 77, pp. 1115- 1130 ,(2005) , 10.1351/PAC200577071115
Sandrine Morandat, Muriel Bortolato, Geneviève Anker, Alain Doutheau, Michel Lagarde, Jean-Paul Chauvet, Bernard Roux, Plasmalogens protect unsaturated lipids against UV-induced oxidation in monolayer Biochimica et Biophysica Acta (BBA) - Biomembranes. ,vol. 1616, pp. 137- 146 ,(2003) , 10.1016/J.BBAMEM.2003.08.001
Jonathan Clayden, Stuart Warren, Stereocontrol in Organic Synthesis Using the Diphenylphosphoryl Group Angewandte Chemie. ,vol. 35, pp. 241- 270 ,(1996) , 10.1002/ANIE.199602411