77202-27-8Relevant articles and documents
High-Atom Economic Approach to Prepare Chiral α-Sulfenylated Ketones
Margalef, Jèssica,Watile, Rahul A.,Rukkijakan, Thanya,Samec, Joseph S. M.
, p. 11219 - 11227 (2019/09/12)
Chiral α-sulfenylated ketones are versatile building blocks, although there are still several limitations with their preparation. Here we report a new two-step procedure, consisting of Pd-catalyzed hydrothiolation of propargylic alcohols followed by an enantioselective Rh isomerization of allylic alcohols. The isomerization reaction is the key step for obtaining the ketones in their enantioenriched form. The new methodology has a high atom economy and induces good to high levels of enantioselectivity; no waste is produced. A mechanism involving a Rh-hydride-enone intermediate is proposed for the isomerization reaction.
Catalytic adaptive recognition of thiol (SH) and selenol (SeH) groups toward synthesis of functionalized vinyl monomers
Ananikov, Valentine P.,Orlov, Nikolay V.,Zalesskiy, Sergey S.,Beletskaya, Irina P.,Khrustalev, Victor N.,Morokuma, Keiji,Musaev, Djamaladdin G.
experimental part, p. 6637 - 6649 (2012/06/15)
An unprecedented sustainable procedure was developed to produce functionalized vinyl monomers H2C=C(R)(FG) starting from a mixture of sulfur and selenium compounds as a functional group donor (FG = S or Se). The reaction serves as a model for e
Palladium Catalysis in Allylic Alkylations and Rearrangements in Pyrimidines
Falck-Pedersen, Mette Lene,Benneche, Tore,Undheim, Kjell
, p. 251 - 258 (2007/10/02)
The regiochemistry of the alkylation of 2-pyrimidinones with ?-allylpalladium complexes from allylic acetates and Pd(0) depends on the substitution pattern in the allylic system.In Pd(II)-catalysed rearrangements of 2-propenyloxypyrimidines the preference for a 1,3-rearrangement or the Claisen 3,3-rearrangement is influenced by the substitution pattern in the allylic system.Pd(0) forms ?-allylpalladium complexes with 2-propenyloxypyrimidines which give rise to rearrangement products.The product ratios in the Pd(II) and Pd(0) rearrangements in unsymmetrically substituted allylic systems are different.The rearrangement reactions, especially the Pd(II) rearrangement, give access to products which are difficult to prepare by direct alkylation.
