116608-40-3Relevant academic research and scientific papers
Oxyallyl Cation Capture via Electrophilic Deborylation of Organoboronates: Access to α, α′-Substituted Cyclic Ketones
Nguyen, Truong N.,Setthakarn, Krit,May, Jeremy A.
, p. 7837 - 7840 (2019)
An umpolung strategy to synthesize α,α′-substituted cyclic ketones through the nucleophilic addition of organoboronates to α-hydroxyl silyl enol ethers is described. The reaction proceeds via the trapping of in situ generated oxyallyl cations via the electrophilic deborylation of C(sp2) and C(sp) borates. This efficient and straightforward method provides direct access to α-substituted silyl enol ethers in high yield with complete regioselectivity. Desilylation in a one-pot procedure provides the corresponding α,α′-disubstituted ketones with high diastereoselectivity.
Effects of Solvent and Residual Water on Enhancing the Reactivity of Six-Membered Silyloxyallyl Cations toward Nucleophilic Addition
Malone, Joshua A.,Cleveland, Alexander H.,Fronczek, Frank R.,Kartika, Rendy
, p. 4408 - 4411 (2016)
A new strategy for the generation of six-membered unsymmetrical silyloxyallyl cations using catalytic mild Br?nsted acid is reported. These reactive intermediates were found to readily undergo direct nucleophilic addition with a broad range of nucleophile
Intramolecular Free Radical Cyclisations onto Enol Ethers. A General Synthesis of α-Alkyl-β-oxy- and α-Methylene-β-oxy-γ-butyrolactones
Begley, Michael J.,Landlow, Mark,Pattenden, Gerald
, p. 1095 - 1106 (2007/10/02)
Radical cyclisation of the enol ether bromoacetals (26), (28a-c), (29), and (37) in the presence of tributylstannane, produces precursors to the β-oxy-γ-butyrolactones (33), (34a-c), (35), and the α-methylene-β-oxy-γ-butyrolactone (39) in high overall yields.By contrast, treatment of (26) and (28a-b) with the cobalt(I) reagent derived from bis(dimethylglyoximato)(pyridine)cobalt(III) chloride (40), followed by oxidation of the intermediates (43) leads to the corresponding unsaturated β-oxy-γ-butyrolactones (42).
