209069-35-2Relevant academic research and scientific papers
Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols
Phipps, Erik J. T.,Rovis, Tomislav
supporting information, (2019/05/06)
We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.
Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude
Fegyverneki, Dániel,Kolozsvári, Natália,Molnár, Dániel,Egyed, Orsolya,Holczbauer, Tamás,Soós, Tibor
supporting information, p. 2179 - 2183 (2019/01/04)
The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.
Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction
Farndon, Joshua J.,Young, Tom A.,Bower, John F.
supporting information, p. 17846 - 17850 (2019/01/04)
In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.
Catalytic Regiodivergent Kinetic Resolution of Allylic Epoxides: A New Entry to Allylic and Homoallylic Alcohols with High Optical Purity
Pineschi, Mauro,Del Moro, Federica,Crotti, Paolo,Di Bussolo, Valeria,Macchia, Franco
, p. 2099 - 2105 (2007/10/03)
A novel regiodivergent kinetic resolution of a series of allylic epoxides with alkylzinc reagents is described. Results demonstrate the potential of chiral copper-phosphoramidite catalysts for enantiomer differentiation of allylic epoxides, allowing a chiral catalyst-stereoregulated synthesis of cyclic allylic and homoallylic alcohols with high optical purities.
Ruthenium-catalyzed isomerization of homoallylic alcohols in water
Wang, Dong,Chen, Dongli,Haberman, John X.,Li, Chao-Jun
, p. 5129 - 5142 (2007/10/03)
Through the catalysis of RuCl2(PPh3)3, the functional groups of homoallylic alcohols are repositioned to give allylic alcohols with controlled regioselectivity. The reaction proceeds most efficiently in an aqueous media. The selectivity in product formation is affected by the reaction temperature and the amount of the catalyst being used. A higher reaction temperature and the use of a smaller amount of the catalyst are preferable for the formation of allylic alcohols. The reaction process was postulated as a tandem olefin migration-allylic rearrangement. Under the same reaction conditions, the functional groups of allylic alcohols undergo allylic rearrangements.
