Conjugate addition of diethyl 1-fluoro-1-phenylsulfonylmethanephosphonate to alpha,beta-unsaturated compounds

0393411 - ÚOCHB 2014 RIV US eng J - Článek v odborném periodiku
Opekar, Stanislav - Pohl, Radek - Eigner, V. - Beier, Petr
Conjugate addition of diethyl 1-fluoro-1-phenylsulfonylmethanephosphonate to alpha,beta-unsaturated compounds.
Journal of Organic Chemistry. Roč. 78, č. 9 (2013), s. 4573-4579. ISSN 0022-3263. E-ISSN 1520-6904
Grant CEP: GA ČR GP203/08/P310
Institucionální podpora: RVO:61388963
Klíčová slova: fluorine * phosphonate * conjugate addition
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 4.638, rok: 2013

Diethyl 1-fluoro-1-phenylsulfonylmethanephosphate (1) in the presence of cesium carbonate undergoes efficient 1,4-addition to Michael acceptors having terminal double bonds such as alpha,beta-unsaturated ketones, esters, sulfones, sulforades, and phosphonates to yield the.,corresponding adducts in good to excellent yields. In the presence of sodium hydride, 1 reacts with alpha,beta-enones to provide gamma-fluoro-gamma-phenylsulfonylenol phosphates arising from 1,4-addition followed by phosphonate to phosphate rearrangement.
Trvalý link: http://hdl.handle.net/11104/0222192