19261-14-4Relevant articles and documents
A new protocol for the acetoxyallylation of aldehydes mediated by indium in THF
Lombardo, Marco,Girotti, Rugiada,Morganti, Stefano,Trombini, Claudio
, p. 2981 - 2983 (2001)
matrix presented A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium
Diastereo- and enantioselective anti-alkoxyallylation employing allylic gem-dicarboxylates as allyl donors via iridium-catalyzed transfer hydrogenation
Han, Soo Bong,Han, Hoon,Krische, Michael J.
supporting information; experimental part, p. 1760 - 1761 (2010/04/25)
(Chemical Equation Presented) Enantioselective transfer hydrogenation of gem-dibenzoate 1e in the presence of aromatic, α,β-unsaturated, or aliphatic aldehydes 2a-i mediated by isopropyl alcohol and employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, 4-cyano-3-nitrobenzoic acid, and (R)-SEGPHOS delivers products of alkoxyallylation 3a-i, 4a, 4e, 4f, and 4i in good isolated yields (62-82%) with good to excellent diastereoselectivities (7:1 to 18:1 dr) and exceptional enantioselectivities (90-99% ee). This protocol provides an alternative to the use of premetalated nucleophiles in carbonyl alkoxyallylation. Copyright
Synthesis of vinyl 1,2-diketones
Habel, Lothar W.,De Keersmaecker, Sigrid,Wahlen, Joos,Jacobs, Pierre A.,De Vos, Dirk E.
, p. 4057 - 4059 (2007/10/03)
A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by 1O2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones.