93862-93-2Relevant academic research and scientific papers
Diastereoselectivity in the reduction of α-oxy- and α-amino-substituted acyclic ketones by polymethylhydrosiloxane
Nadkarni, Durgesh,Hallissey, James,Mojica, Carlos
, p. 594 - 596 (2007/10/03)
Diastereoselectivity in the reduction of α-alkoxy-, α-acyloxy-, and α-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of α-alkoxy, α-acyloxy, and α-dialkylamino ketones. Reduction of α-monoalkylamino ketone proceeded in anti-selective manner with moderate selectivity. The observed selectivity is explained based on Felkin-Anh and Cram-chelate models.
Manganese(III)-Mediated γ-Lactone Annulation
Fristad, William E.,Peterson, John R.
, p. 10 - 18 (2007/10/02)
The annulation of a γ-lactone ring onto an alkene by manganese(III) acetate oxidation of acetic acid was investigated.The regioselectivity of addition to unsymmetrically substituted alkenes is reported along with the stereoselectivity of addition to various acyclic and cyclic alkenes.Alkenes with ionization potentials above 8.2 eV were found to react in good yield.The role of acetic anhydride in these reactions was studied, and it was shown to be oxidized faster than acetic acid and also led to different products.The fate of oxidized acetic acid or anhydridein the absence of suitable acceptor molecule has also been quantitatively identified.The relationship of enolizability, or C-H acidity, of the carboxylic acid being oxidized was established quantitatively.
