88246-66-6Relevant academic research and scientific papers
An efficient α-hydroxylation of carbonyls using the HOF·CH3CN complex
Dayan, Sharon,Bareket, Yifat,Rozen, Shlomo
, p. 3657 - 3664 (2007/10/03)
The complex HOF·CH3CN, made directly from fluorine and aqueous acetonitrile, was used for α-hydroxylation of various ketones, esters and acids via their trimethyl silyl enol ethers. The reaction is usually complete in a few minutes at room temperature or below and has high yields.
α-SILYL TRIMETHYLSILYLESTERS FROM ALIPHATIC CARBOXYLIC ACID DIANIONS
Bellassoued, M.,Dubois, J. E.,Bertounesque, E.
, p. 263 - 266 (2007/10/02)
The synthesis of α-silyl trimethylsilyl esters from aliphatic carboxylic acid dianions is reported.The results indicate kinetic and thermodynamic control of silylation of acid dianions.
METHYLENECYCLOHEXANE ANNULATION. TOTAL SYNTHESIS OF (+/-)-AXAMIDE-1, (+/-)-AXISONITRILE-1, AND THE CORRESPONDING C-10 EPIMERS
Piers, Edward,Yeung, Bik Wah Anissa,Rettig, Steven J.
, p. 5521 - 5536 (2007/10/02)
Conjugate addition of 2-(5-chloro-1-pentenyl)magnesium bromide (12) to 2-methyl-2-cyclopenten-1-one (6), followed by intramolecular alkylation of the resultant product, afforded (85percent) the bicyclic ketone 7, which was transformed (77percent) into the enone 16.Titanium tetrachloride-catalyzed conjugate addition of 3-methyl-1,1-bis(trimethylsiloxy)-1-butene to 16 gave (93percent) a 3:2 mixture of the keto acids 20 and 21, which were separated.Compound 20, the stereochemistry of wich was confirmed by a single-crystal X-ray analysis, was converted into (+/-)-axamide-1 (1) and (+/-)-axisonitrile-1 (2), while 21 was transformed into the corresponding C-10 epimers 8 and 9, respectively.
Total syntheses of the sesquiterpenoids (+/-)-axamide-1, (+/-)-axisonitrile-1, and the corresponding C-10 epimers
Piers, Edward,Yeung, Bik Wah Anissa
, p. 2475 - 2477 (2007/10/02)
Total syntheses of (+/-)-axamide-1 (1), (+/-)-axisonitrile-1 (2), and the corresponding C-10 epimers 16 and 17 are described.The key steps of the synthetic sequence involve methylenecyclohexane annulation of 2-methyl-2-cyclopenten-1-one and TiCl4-catalyzed conjugate addition of 3-methyl-1,1-bis(trimethylsiloxy)-1-butene to the bicyclic enone 8.
