133967-39-2Relevant articles and documents
Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates
Hazelden, Ian R.,Carmona, Rafaela C.,Langer, Thomas,Pringle, Paul G.,Bower, John F.
supporting information, p. 5124 - 5128 (2018/03/26)
Ligand-enabled aza-Heck cyclizations and cascades of N-(pentafluorobenzoyloxy)carbamates are described. These studies encompass the first examples of efficient non-biased 6-exo aza-Heck cyclizations. The methodology provides direct and flexible access to carbamate protected pyrrolidines and piperidines.
Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System
Fujita, Shoji,Abe, Masanori,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 3822 - 3825 (2015/08/18)
A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.
Diastereoselective carbocyclization of 1,6-heptadienes triggered by rhodium-catalyzed activation of an olefinic C-H bond
Aissa, Christophe,Ho, Kelvin Y. T.,Tetlow, Daniel J.,Pin-No, Maria
supporting information, p. 4209 - 4212 (2014/05/06)
The use of α,ω-dienes as functionalization reagents for olefinic carbon-hydrogen bonds has been rarely studied. Reported herein is the rhodium(I)-catalyzed rearrangement of prochiral 1,6-heptadienes into [2,2,1]-cycloheptane derivatives with concomitant creation of at least three stereogenic centers and complete diastereocontrol. Deuterium-labeling studies and the isolation of a key intermediate are consistent with a group-directed C-H bond activation, followed by two consecutive migratory insertions, with only the latter step being diastereoselective. Folding alkenes: Described is the first example of a rhodium(I)-catalyzed functionalization of an olefinic C-H bond with a 1,6-heptadiene reagent. This carbocyclization is completely diastereoselective and creates at least three stereogenic centers from simple prochiral substrates. The directing group can easily be converted into other functional groups.
The Regio- and Stereoselectivities of the Reaction of Allyl Acetates and Silyl Ketene Acetals Catalyzed by Pd(0) Complexes: A New Route to Cyclopropane Derivatives
Carfagna, C.,Mariani, L.,Musco, A.,Sallese, G.,Santi, R.
, p. 3924 - 3927 (2007/10/02)
Pd(0) complexes of chelating phosphines catalyzed the coupling of allyl acetates and ketene silyl acetals to yield α-allylated carboxylic acid esters.Unexpectedly alkylation of the central carbon atom (C2) of the allyl groups was also observed with concomitant formation of cyclopropane derivatives.In both cases the silyl enolate attacked the allyl group from the side opposite Pd.The yield of the reaction was sensitive to the nature of the ligand coordinated with palladium.The 1,1'-bis(diphenylphosphino)ferrocene-Pd complex was the most effective catalyst.
