57955-48-3Relevant articles and documents
Copper-catalyzed desymmetrization of prochiral 4,4-disubstituted cyclopentenes: Via a site-selective allylic oxidation: A concise total synthesis of untenone A
Gui, Qingwen,Wang, JuanJuan,Ng, Sean,Dancevic, Anja,Wright, Timothy B.,Andrew Evans
supporting information, p. 12368 - 12371 (2019/10/19)
The desymmetrization of prochiral 4,4-disubstituted cyclopentenes via a site-selective copper-catalyzed allylic oxidation is described. This study provides a direct comparison of a series of known methods for allylic oxidation, and thus identifies ligand-free copper(i) iodide as the optimal catalyst for this particular process. Notably, this work offers a convenient approach to the preparation of γ-quaternary α,β-unsaturated cyclopentenones, which permits an efficient three-step total synthesis of (±)-untenone A.
Tandem olefin metathesis/hydrogenation at ambient temperature: Activation of ruthenium carbene complexes by addition of hydrides
Schmidt, Bernd,Pohler, Michael
, p. 2512 - 2517 (2007/10/03)
Sodium hydride activates ruthenium carbene complexes to catalyze hydrogenation reactions subsequent to ring closing olefin metathesis. Under these conditions, hydrogenation of cyclopentenols proceeds smoothly at ambient temperature and under 1 atm of hydrogen in toluene. An alternative protocol was developed that involves the formation of hydrogen in situ by reaction of excess sodium hydride with protic functional groups and water.
CERIUM CHLORIDE-PROMOTED NUCLEOPHILIC ADDITION OF GRIGNARD REAGENTS TO KETONES AN EFFICIENT METHOD FOR THE SYNTHESIS OF TERTIARY ALCOHOLS
Imamoto, Tsuneo,Takiyama, Nobuyuki,Nakamura, Kamikazu
, p. 4763 - 4766 (2007/10/02)
In the presence of anhydrous cerium(III) chloride, Grignard reagents react with ketones to afford addition products in high yields, even though the substrates are susceptible to abnormal reactions with Grignard reagents alone.
