Published in Russian Chemical Bulletin
The review summarizes the data on the synthesis of heterocyclic compounds by means of [3,3]-sigmatropic transformations, which include the Fischer, Claisen, and Cope rearrangements, as well as their numerous variations. These reactions have proved to be a convenient and efficient method for the synthesis of complex and poorly available heterocyclic...
Published in Angewandte Chemie (International ed. in English)
The first examples of Lewis base adducts of the parent boraphosphaketene (H2 B-PCO) and their cyclodimers are prepared. One of these adducts is shown to undergo mild decarbonylation and phosphinidene insertion into a B-C bond of a borole, forming very rare examples of 1,2-phosphaborinines, B/P isosteres of benzene. The strong donor properties of th...
Published in Angewandte Chemie (International ed. in English)
The asymmetric synthesis of β2,2 -amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing β2,2 -amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a ca...
Published in Molecules
Inversions in the periselectivity of formal aza-Diels–Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was...
Published in Angewandte Chemie (International ed. in English)
Vinylcyclopropanes (VCPs) are commonly used in transition-metal-catalyzed cycloadditions, and the utilization of their recently realized reactivities to construct new cyclic architectures is of great significance in modern synthetic chemistry. Herein, a palladium-catalyzed, visible-light-driven, asymmetric [5+2] cycloaddition of VCPs with α-diazoke...
The thermal 6π aza-Diels−Alder cycloadditions between α-oxoketenes, in situ derived from a thermally induced Wolff rearrangement of 2-diazo-1,3-diketones, and N-(5-pyrazolyl)imines as prototypical electron-rich 2-azadienes lead to two distinct sets of products, essentially as a function of the nature of the α-oxoketenes involved. For instance, cycl...
Published in Russian Journal of Organic Chemistry
AbstractThe enantiospecific synthesis of 3-acetoxy-trans-β-lactams via the Staudinger [2+2] cycloaddition reaction of polyaromatic imines with bicyclic (+)-car-3-ene was investigated. The sterically hindered polyaromatic substituent at the N1 position in the imines plays a significant role, directing the cycloaddition reaction to stereoselective fo...
The thermal 6π aza-Diels−Alder cycloadditions between α-oxoketenes, in situ derived from a thermally induced Wolff rearrangement of 2-diazo-1,3-diketones, and N-(5-pyrazolyl)imines as prototypical electron-rich 2-azadienes lead to two distinct sets of products, essentially as a function of the nature of the α-oxoketenes involved. For instance, cycl...
Inversions in the periselectivity of formal aza-Diels–Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was...
Published in Macromolecular rapid communications
In this report, highly active metallocene initiators are used for the polymerization of a ketene monomer, dimethylketene, which typically contains two adjacent double bonds (R2 CCO). By using the methylzirconocene methyltriarylborate complex (Cp2 ZrMe+ MeB(C6 F5 )3 - ) as the activation system, associated with the possible cleavage of CC and CO...
