53857-10-6Relevant articles and documents
CuH-catalyzed enantioselective intramolecular reductive aldol reactions generating three new contiguous asymmetric stereocenters
Lipshutz, Bruce H.,Amorelli, Benjamin,Unger, John B.
supporting information; experimental part, p. 14378 - 14379 (2009/02/08)
Treatment of β,β-disubstituted-α,β-unsaturated ketones bearing a ketone residue with in situ generated, catalytic CuH ligated by a nonracemic ligand leads to three newly created adjacent chiral centers. Excellent des and ees are obtained for several examples studied. Copyright
Photoaddition of styrene on certain β-polyketones
Mansri, Ali,Casals, Pierre-Francois,Fan, Bo Tao,Lapluye, Gerard
, p. 247 - 252 (2007/10/02)
The irradiation of 1,5-diphenylpentane-1,3,5-trione 1 and 1-phenylhexane-1,3,5-trione 2 at λ > 290 nm with styrene gives products of double photo-addition: 1,2,6,9-tetraphenylnonane-1,5,9-trione 5 and 1,2,6-triphenyldecane-1,5,9-trione 6, respectively.Under the same conditions with λ > 220 nm, 2-(3-oxo-3-phenylpropionyl)indane-1,3-dione 3 and 2-(3-oxobutyryl)indane-1,3-dione 4 give only products of simple photoaddition: 4-(3-oxo-3-phenylpropionyl)-2-phenylbenzocycloheptane-1,5-dione 7 and 4-(3-oxobutyryl)-2-phenylbenzocycloheptane-1,5-dione 8, respectively.The regiospecificity previously observed with the β-diketones is not a general rule for these β-triketones.The phenyl group in position 6 (products 5 and 6) is not in the α-position of the benzoyl group.The δ-triketones obtained are characterized using β-diketonic models, which are prepared by a simple sequence.Observations of products 7 and 8 show that styrene reacts with the cyclic enol only.This work may be considered as a model study for the prediction of the behavior of triketones 1, 2, 3 and 4 in the side chain of polymeric compounds.Keywords: photoaddition / styrene / β-polyketones / stereoselectivity
2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane: New masked lithium bishomoenolates in the synthesis of bifunctionalized compounds
Ramon, Diego J.,Yus, Miguel
, p. 3763 - 3766 (2007/10/02)
2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane (2) are prepaned by lithiation of the corresponding chlorinated precursors with lithium naphthalenide at -78°C. The reaction of these masked bishomoenolates with different electrophiles yie