91711-97-6Relevant articles and documents
Enantio- and regioselective conjugate addition of organometallic reagents to linear polyconjugated nitroolefins
Tissot, Matthieu,Alexakis, Alexandre
, p. 11352 - 11363 (2013/09/02)
The copper-catalysed conjugate addition of trialkylaluminium and dialkylzinc reagents to polyconjugated nitroolefins (nitrodiene and nitroenyne derivatives) is reported. A reversed Josiphos ligand L7 allows for the selective 1,4- or 1,6-addition with high enantioselectivities. Copyright
Synthesis of E-α,β-unsaturated ketones with complete stereoselectivity via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium dichloride
Concellón, José M.,Rodríguez-Solla, Humberto,Concellón, Carmen,Díaz, Pamela
, p. 837 - 840 (2007/10/03)
E-α,β-Unsaturated ketones can be obtained with complete E-selectivity by a sequential reaction of dichloroketones with a variety of aldehydes. This transformation was promoted by SmI2, SmI2 in the presence of FeCl3 or CrCl2. The best results were obtained when CrCl2 was used as the metallating agent. A mechanism based on a successive aldol-type reaction and a β-elimination is proposed to explain these results. Georg Thieme Verlag Stuttgart.
Acyclic Stereoselection. 22. Diastereofacial Selectivity in the Lewis Acid Mediated Reactions of Allylsilanes with Chiral Aldehydes and Enones
Heathcock, Clayton H.,Kiyooka, Syun-ichi,Blumenkopf, Todd A.
, p. 4214 - 4223 (2007/10/02)
The Lewis acid mediated reactions of chiral aldehydes 1-4 and enones 5-8 with allylsilanes 9 and 10 have been investigated.With aldehyde 1 and enones 5-7, modest diastereofacial preferences are seen, in the sense predicted by application of Felkin's model for asymmetric induction.Aldehydes 2-4 and enone 8 appear to react by way of chelated intermediates.With these four compounds, the diastereofacial preferences are rather large and are in the sense that is consistend with attack of the allylsilane on the least hindered face of the chelated intermediate.In the reaction of the trans and cis enones 6 and 8 with allyltrimethylsilane, a dramatic reversal of diastereofacial preference is observed; enone 6 gives a 84:14 ratio of products, while enone 8 provides a 10:90 mixture of the same products.