354530-05-5Relevant academic research and scientific papers
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%.
Cram's Rule for Radical Reactions
Giese, Bernd,Damm, Wolfgang,Dickhaut, Joachim,Wetterich, Frank,Sun, Shunneng,Curran, Dennis P.
, p. 6097 - 6100 (2007/10/02)
Addition of tris(trimethylsilyl)silyl radicals to chiral ketones 1 yields tert. carbon centered radicals 4 that give predominantly Cram products in hydrogen atom abstraction reactions.Analogous sec. acyloxyalkyl radicals undergo radical C,D- and C,C-bond forming reactions that also follow Cram's rule.
