10035-97-9Relevant articles and documents
Application of Rh(l)-Catalyzed C - H Bond Activation to the Ring Opening of 2-Cycloalkenones in the Presence of Amines
Jun, Chul-Ho,Moon, Choong Woon,Lim, Sung-Gon,Lee, Hyuk
, p. 1595 - 1597 (2002)
(matrix presented) Herein described is the application of the Rh(l)-catalyzed C-H bond activation to the ring-opening of 2-cycloalkenones in the presence of cyclohexylamine. This reaction includes the C-C double bond cleavage of 2-cycloalkenones through the conjugate addition of cyclohexylamine followed by the retro-Mannich-type fragmentation. The resulting ring-opened intermediates subsequently underwent either chelation-assisted hydroacylation to afford a ring-opened dicarbonyl compound or β-alkylation via a ring contraction.
Concannon,Ciabattoni
, p. 3284,3285, 3288 (1973)
Recoverable chiral sulfoxides for asymmetric synthesis: application to stereoselective carbonyl reduction and the asymmetric synthesis of allylic alcohols
Butlin, Roger J.,Linney, Ian D.,Mahon, Mary F.,Tye, Heather,Wills, Martin
, p. 95 - 106 (2007/10/03)
The enantiomerically pure cyclic sulfinamide S(S)R-(+)-3 reacts with the sodium enolates of ketones to give the corresponding homochiral sulfoxides.Reduction of the carbonyl group in these products may be achieved using a variety of reducing agents the best of which were DIBAL-H or DIBAL-H/ZnBr2, which give complementary products of high diastereomeric excess.Reduction of the hydroxy sulfoxides with Raney nickel proceeds in low yield and causes partial racemisation of the products.However the combined use of a durected reduction followed by a facile sulfenic acid elimination provides a synthesis of allylic alcohols in high enentiomeric excess.