26755-25-9Relevant academic research and scientific papers
Aldol-Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivatives
Sedano, Carlos,Virumbrales, Cintia,Suárez-Pantiga, Samuel,Sanz, Roberto
supporting information, p. 3725 - 3734 (2021/07/02)
α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol-Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes.
Sodium iodide-catalyzed direct α-alkoxylation of ketones with alcohols via oxidation of α-iodo ketone intermediates
Zhu, Cuiju,Zhang, Yuanfei,Zhao, Huaiqing,Huang, Shijun,Zhang, Min,Su, Weiping
supporting information, p. 331 - 338 (2015/02/19)
The direct α-alkoxylation of ketones with alcohols via a sodium iodide-catalyzed oxidative cross-coupling has been developed. This protocol enables a range of alkyl aryl ketones to cross couple with an array of alcohols in synthetically useful yields. The mechanistic studies provided solid evidence supporting that an α-iodo ketone was a key reaction intermediate, being converted into an α-alkoxylated ketone via further oxidation to a hypervalent iodine species rather than a common nucleophilic substitution, and was generated from the ketone starting material via a radical intermediate. These new mechanism insights should have an effect on the design of iodide-catalyzed oxidative cross-coupling reactions between nucleophiles.
A facile synthesis of secondary α-alkoxy or α-acetoxy aromatic ketones
Lee, Jong Chan,Hong, Taiyoung
, p. 4085 - 4090 (2007/10/03)
The treatment of HNIB with aromatic ketones and subsequent solvolysis using alcohol or acetic acid in one-pot system makes it possible to give corresponding secondary α-alkoxy or α-acetoxy ketones in high yields.
The conjugate addition of higher-order organocuprates to α-methoxyenones
Soderquist, John A.,Rosado, Izander
, p. 4451 - 4452 (2007/10/02)
The conjugate addition of higher-order organocuprates (Lipshutz reagents) at low temperature (-78° C) to α-methoxyenones (4) provides the corresponding β-substituted α-methoxy ketones (5) in 74-90% isolated yields.
