68318-17-2Relevant academic research and scientific papers
An efficient synthesis of α-branched enones
Kummer, David A.,Brenneman, Jehrod B.,Martin, Stephen F.
, p. 1431 - 1433 (2007/10/03)
A new method for preparing α-branched enones from carboxylic acid derivatives is reported. The procedure commenced by the reaction of N,O-dimethylamides with a masked acyl anion equivalent, followed by the addition of (trimethylsilyl-methyl)cerium dichloride to give intermediates that undergo Lewis acid mediated olefination to produce enol ethers that are then hydrolyzed to afford simple α-branched enones in high overall yields.
Baker's yeast reduction of α-methyleneketones
Siqueira Filho, Ezequias P.,Rodrigues, J.Augusto R.,Moran, Paulo J.S.
, p. 847 - 852 (2007/10/03)
The bioreduction of α-methyleneketones, R1C(=O)C(=CH2)R2 (R1 = Me, Et, Pr, iso-Bu, Ph, CH2CH2Ph; R2 = Cl, Me, Et, n-Pr, iso-Pr, n-Bu, n-C6H13, Ph, CH2Ph), was mediated by baker's yeast (Saccharomyces cerevisiae) to obtain the corresponding α-methylketones. The R1 and R2 groups had a significant influence on the rate and enantioselectivity of the reductions. The rate of C=C bond reduction was higher than that of C=O bond reduction. Only α-methyleneketones having R1 = Me yielded α-methylketones in high enantioselectivity with e.e.s of 88-99%.
Asymmetric Reduction of Carbon-Carbon Double Bonds of Conjugated Enones with Fermenting Bakers' yeast
Sakai, Takashi,Matsumoto, Syuji,Hidaka, Syukou,Imajo, Norihisa,Tsuboi, Sadao,Utaka, Masanori
, p. 3473 - 3475 (2007/10/02)
Bakers' yeast reduction of α-substituted or β,β-disubstituted α,β-unsaturated ketones gave saturated chiral ketones with excellent optical purity, while the β,β-disubstituted derivatives remains intact.
