92694-77-4Relevant articles and documents
Generation of rhodium enolates via retro-aldol reaction and its application to regioselective aldol reaction
Murakami, Kei,Ohmiya, Hirohisa,Yorimitsu, Hideki,Oshima, Koichiro
, p. 2388 - 2390 (2008/09/18)
Retro-aldol reactions of β-hydroxy ketones take place under rhodium catalysis, leading to regioselective formation of the corresponding rhodium enolates. The enolates react with aldehydes in situ to afford the corresponding aldol adducts in high yields.
Stereoselective 1,4-hydroboration of acyclic (E)-α,β-unsaturated ketones with dialkylboranes. Synthesis of (Z)-vinyloxyboranes
Boldrini, Gian Paolo,Bortolotti, Michele,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 1229 - 1232 (2007/12/18)
Dialkylboranes add to acyclic disubstituted (E)-α,β-unsaturated ketones in a 1,4-fashion affording (Z)-vinyloxyboranes as major or sole products. The stereochemical outcome of the hydroboration reaction is consistent with a concerted pericyclic mechanism. The intermediate vinyloxyboranes can be trapped with aldehydes to give virtually pure syn β-hydroxyketones.
A New Approach to (Z)-Vinyloxyboranes via 1,4 Hydroboration of (E)-α,β-Unsaturated Ketones. Synthesis of syn Aldols
Boldrini, Gian Paolo,Mancini, Fabrizio,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 1680 - 1681 (2007/10/02)
(Z)-Vinyloxy boranes are obtained via 1,4-hydroboration of acyclic disubstituted (E)-α,β-unsaturated ketones with dicyclohexylborane or diisopinocampheylborane in tetrahydrofuran, CH2Cl2 or CHCl3 at 20 deg C; treatment of the hydroboration mixture with an aldehyde allows pure syn aldols to be synthesized in good yields, and in excellent enantiomeric excesses, using the latter borane.
