The Experts below are selected from a list of 300 Experts worldwide ranked by ideXlab platform
Igor V. Trushkov - One of the best experts on this subject based on the ideXlab platform.
-
lewis acid triggered vinylcyclopropane cyclopentene rearrangement
Journal of Organic Chemistry, 2017Co-Authors: Olga A Ivanova, Alexey O. Chagarovskiy, Vasiliy D. Krasnobrov, I. I. Levina, Alexey Shumsky, Igor V. TrushkovAbstract:We report a mild Lewis acid induced isomerization of donor–acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s) at the adjacent positions, into substituted cyclopentenes. We have found that 1,1,2-trisubstituted cyclopent-3-enes were exclusively obtained in yield of 51–99% when cyclopropanes with a 2-substituted alkenyl group as a donor underwent isomerization. For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes or isomeric cyclopent-2-enes having two acceptor groups at the C(1) atom were formed, with the reaction selectivity being determined by the applied Lewis acid. We have shown that the reactivity of the donor–acceptor cyclopropane increases with the increase of the electron-donating character of (hetero)aromatic group attached to the alkenyl moiety. The synthetic utility of the developed methodology was also demonstrated through the synthesis of polysubstituted cyclopentane and piperidine derivatives.
-
Lewis Acid Triggered Vinylcyclopropane–Cyclopentene Rearrangement
Journal of Organic Chemistry, 2017Co-Authors: Olga A Ivanova, Alexey O. Chagarovskiy, Vasiliy D. Krasnobrov, I. I. Levina, Alexey Shumsky, Igor V. TrushkovAbstract:We report a mild Lewis acid induced isomerization of donor–acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s) at the adjacent positions, into substituted cyclopentenes. We have found that 1,1,2-trisubstituted cyclopent-3-enes were exclusively obtained in yield of 51–99% when cyclopropanes with a 2-substituted alkenyl group as a donor underwent isomerization. For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes or isomeric cyclopent-2-enes having two acceptor groups at the C(1) atom were formed, with the reaction selectivity being determined by the applied Lewis acid. We have shown that the reactivity of the donor–acceptor cyclopropane increases with the increase of the electron-donating character of (hetero)aromatic group attached to the alkenyl moiety. The synthetic utility of the developed methodology was also demonstrated through the synthesis of polysubstituted cyclopentane and piperidine derivatives.
-
formal 3 2 cycloaddition of donor acceptor cyclopropanes to 1 3 dienes cyclopentane assembly
Journal of Organic Chemistry, 2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed.
-
Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed
Olga A Ivanova - One of the best experts on this subject based on the ideXlab platform.
-
lewis acid triggered vinylcyclopropane cyclopentene rearrangement
Journal of Organic Chemistry, 2017Co-Authors: Olga A Ivanova, Alexey O. Chagarovskiy, Vasiliy D. Krasnobrov, I. I. Levina, Alexey Shumsky, Igor V. TrushkovAbstract:We report a mild Lewis acid induced isomerization of donor–acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s) at the adjacent positions, into substituted cyclopentenes. We have found that 1,1,2-trisubstituted cyclopent-3-enes were exclusively obtained in yield of 51–99% when cyclopropanes with a 2-substituted alkenyl group as a donor underwent isomerization. For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes or isomeric cyclopent-2-enes having two acceptor groups at the C(1) atom were formed, with the reaction selectivity being determined by the applied Lewis acid. We have shown that the reactivity of the donor–acceptor cyclopropane increases with the increase of the electron-donating character of (hetero)aromatic group attached to the alkenyl moiety. The synthetic utility of the developed methodology was also demonstrated through the synthesis of polysubstituted cyclopentane and piperidine derivatives.
-
Lewis Acid Triggered Vinylcyclopropane–Cyclopentene Rearrangement
Journal of Organic Chemistry, 2017Co-Authors: Olga A Ivanova, Alexey O. Chagarovskiy, Vasiliy D. Krasnobrov, I. I. Levina, Alexey Shumsky, Igor V. TrushkovAbstract:We report a mild Lewis acid induced isomerization of donor–acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s) at the adjacent positions, into substituted cyclopentenes. We have found that 1,1,2-trisubstituted cyclopent-3-enes were exclusively obtained in yield of 51–99% when cyclopropanes with a 2-substituted alkenyl group as a donor underwent isomerization. For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes or isomeric cyclopent-2-enes having two acceptor groups at the C(1) atom were formed, with the reaction selectivity being determined by the applied Lewis acid. We have shown that the reactivity of the donor–acceptor cyclopropane increases with the increase of the electron-donating character of (hetero)aromatic group attached to the alkenyl moiety. The synthetic utility of the developed methodology was also demonstrated through the synthesis of polysubstituted cyclopentane and piperidine derivatives.
-
formal 3 2 cycloaddition of donor acceptor cyclopropanes to 1 3 dienes cyclopentane assembly
Journal of Organic Chemistry, 2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed.
-
Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed
Alexey O. Chagarovskiy - One of the best experts on this subject based on the ideXlab platform.
-
lewis acid triggered vinylcyclopropane cyclopentene rearrangement
Journal of Organic Chemistry, 2017Co-Authors: Olga A Ivanova, Alexey O. Chagarovskiy, Vasiliy D. Krasnobrov, I. I. Levina, Alexey Shumsky, Igor V. TrushkovAbstract:We report a mild Lewis acid induced isomerization of donor–acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s) at the adjacent positions, into substituted cyclopentenes. We have found that 1,1,2-trisubstituted cyclopent-3-enes were exclusively obtained in yield of 51–99% when cyclopropanes with a 2-substituted alkenyl group as a donor underwent isomerization. For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes or isomeric cyclopent-2-enes having two acceptor groups at the C(1) atom were formed, with the reaction selectivity being determined by the applied Lewis acid. We have shown that the reactivity of the donor–acceptor cyclopropane increases with the increase of the electron-donating character of (hetero)aromatic group attached to the alkenyl moiety. The synthetic utility of the developed methodology was also demonstrated through the synthesis of polysubstituted cyclopentane and piperidine derivatives.
-
Lewis Acid Triggered Vinylcyclopropane–Cyclopentene Rearrangement
Journal of Organic Chemistry, 2017Co-Authors: Olga A Ivanova, Alexey O. Chagarovskiy, Vasiliy D. Krasnobrov, I. I. Levina, Alexey Shumsky, Igor V. TrushkovAbstract:We report a mild Lewis acid induced isomerization of donor–acceptor cyclopropanes, containing an alkenyl moiety and diverse electron-withdrawing group(s) at the adjacent positions, into substituted cyclopentenes. We have found that 1,1,2-trisubstituted cyclopent-3-enes were exclusively obtained in yield of 51–99% when cyclopropanes with a 2-substituted alkenyl group as a donor underwent isomerization. For cyclopropanes bearing a trisubstituted alkenyl group either the corresponding cyclopent-3-enes or isomeric cyclopent-2-enes having two acceptor groups at the C(1) atom were formed, with the reaction selectivity being determined by the applied Lewis acid. We have shown that the reactivity of the donor–acceptor cyclopropane increases with the increase of the electron-donating character of (hetero)aromatic group attached to the alkenyl moiety. The synthetic utility of the developed methodology was also demonstrated through the synthesis of polysubstituted cyclopentane and piperidine derivatives.
-
formal 3 2 cycloaddition of donor acceptor cyclopropanes to 1 3 dienes cyclopentane assembly
Journal of Organic Chemistry, 2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed.
-
Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed
Dieter Hoppe - One of the best experts on this subject based on the ideXlab platform.
-
Asymmetric Synthesis of 2-Alkenyl-1-cyclopentanols via Tin−Lithium Exchange and Intramolecular Cycloalkylation
Organic letters, 2002Co-Authors: Guido Christoph, Dieter HoppeAbstract:We report a method for the synthesis of chiral Cyclopentanes using tin−lithium exchange and cycloalkylation reactions. The sec-butyllithium/(−)-sparteine-mediated deprotonation of an alkyl carbamate and subsequent substitution furnishes a highly enantioenriched stannane as a stable carbanion equivalent. It was transformed into suitable cyclization precursors, which underwent tin−lithium exchange and stereoselective cycloalkylation when reacted with n-butyllithium, giving highly enantioenriched Cyclopentanes in very good yields. A kinetic resolution was observed with a higher substituted stannane.
-
asymmetric synthesis of 2 alkenyl 1 cyclopentanols via tin lithium exchange and intramolecular cycloalkylation
Organic Letters, 2002Co-Authors: Guido Christoph, Dieter HoppeAbstract:We report a method for the synthesis of chiral Cyclopentanes using tin−lithium exchange and cycloalkylation reactions. The sec-butyllithium/(−)-sparteine-mediated deprotonation of an alkyl carbamate and subsequent substitution furnishes a highly enantioenriched stannane as a stable carbanion equivalent. It was transformed into suitable cyclization precursors, which underwent tin−lithium exchange and stereoselective cycloalkylation when reacted with n-butyllithium, giving highly enantioenriched Cyclopentanes in very good yields. A kinetic resolution was observed with a higher substituted stannane.
Mikhail Ya Melnikov - One of the best experts on this subject based on the ideXlab platform.
-
formal 3 2 cycloaddition of donor acceptor cyclopropanes to 1 3 dienes cyclopentane assembly
Journal of Organic Chemistry, 2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed.
-
Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
2015Co-Authors: Ekaterina M Budynina, Alexey O. Chagarovskiy, Yuri K. Grishin, Igor V. Trushkov, Olga A Ivanova, Mikhail Ya MelnikovAbstract:We report a new simple method to access highly substituted Cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized Cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor–acceptor cyclopropanes with dienes, has been developed
