Anatoly V. Ignatenko

Preparation of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines by reductive trans-2,6-dialkylation of pyridine. Synthesis of (±)-epidihydropinidine

Abstract A convenient method for the preparation of the title compounds involving the sequential treatment of pyridine with RLi ( R = Alk , Ar ), triallylborane and methanol is developed.

trans-cis-Isomerization of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines on heating with triallylborane. Synthesis of (±)-dihydropinidine

Abstract A convenient method for isomerization of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines into the corresponding cis-isomers is presented.

Reductive 1,2‐Allylboration of Indoles by Triallyl‐ and Triprenylborane − Synthesis of 2‐Allylated Indolines

Indoles undergo reductive α-allylation upon treatment with allylic boranes (triallyl- and triprenylborane) to give, after deboronation, the corresponding 2-allylated indolines in 70−85% yield. 1,2-Addition of the allylboron fragment to heterocycles occurs with full rearrangement of the allylic moiety. Reductive prenylboration of 3-substituted indoles, as well as allylboration of 3-isopropylindole, with All3B proceed stereoselectively to produce trans-2,3-disubstituted indolines only, while similar reactions of triallylborane with 3-R-indoles, containing a primary group R, afford a mixture of trans (86−92%) and cis isomers (8−14%). From 1-deuterioindole and triallylborane, a mixture of cis- and trans-2-allyl-3-deuterioindole in a ratio of 1:1 was obtained. Proposed mechanism of the general reaction involves intermediate formation of 3H-indole tautomers followed by fast allylboration of the C=N bond. Structures of trans-indolines 3b and 3c were confirmed by X-ray analysis.

Codimerization of allylacetone with vinyl ketones catalyzed by [RhCl(C2H4)2]2 - SnCl2

Abstract Codimerization of allylacetone with different vinyl ketones catalyzed by [RhCl (C 2 H 4 ) 2 ] 2 - SnCl 2 leads to the formation of 1,5- and 1,7-diketones.

Reductive diallylation of natural amino acids with triallylborane. The first synthesis of chiral 1,1,-diallyl-2-amino alcohols and their cyclization into optically active pyrrolidines.

Abstract The titled amino alcohols are obtained by treatment of chiral amino acids with triallylborane. Electrophylic iodocyclization of the alcohols leads to pyrrolidine derivatives.

Catalytic codimerization of α,β-with γ,δ-unsaturated ketones : novel stereoselective method of the synthesis of functionalized 8-oxabicyclo[3.2.1]octanes

Functionalized 8-oxabicyclo[3.2.1]octanes (3a-e) were obtained in one stage from vinyl ketones and 5-methylhex-5-en-2-one or 1-phenyl-4-methylpent-4-en-1-one in the presence of the catalytic system [RhCl(C2H4)2]2 - SnCl2.

Catalytic addition—cyclization of alkyl ketones with 4-methyl-1-phenyl-4-penten-1-one.

Abstract Substituted 2-(β-oxoalkyl)tetrahydrofurans were obtained in one-step aldol-type reaction from alkyl ketones and 4-methyl-1-phenyl-4-penten-1-one in the presence of a catalytic system [RhCl(C2H4)2]2SnCl2