98%
921
2 minutes
20
Terminal (het)arylacetylenes react (KOBu/DMSO, 60 °C, 1 h) with -allyl ketimines to afford 2-(het)aryl-4-(het)arylmetyl-5-ethylpyrroles in up to 71% yield as a result of the interaction of acetylenic and azadienic carbanions with C=N and C≡C bonds. This new reaction opens a one-pot access to synthetically and pharmaceutically prospective compounds.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.5c01545 | DOI Listing |
Org Lett
May 2025
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
Terminal (het)arylacetylenes react (KOBu/DMSO, 60 °C, 1 h) with -allyl ketimines to afford 2-(het)aryl-4-(het)arylmetyl-5-ethylpyrroles in up to 71% yield as a result of the interaction of acetylenic and azadienic carbanions with C=N and C≡C bonds. This new reaction opens a one-pot access to synthetically and pharmaceutically prospective compounds.
View Article and Find Full Text PDFOrg Lett
February 2025
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165, China.
The enantioselective ring-opening reactions of methylenecyclopropanes (MCPs) involving C-C bond activation via oxidative addition of transition metals have been rarely reported. Here, we disclose a Pd/Cu-catalyzed enantio- and regioselective coupling between cyclic imino esters and MCPs to produce α-allylated 2-pyrrole derivatives. In this reaction, azomethine ylide formed by a chiral copper catalyst with ketimine ester would serve as a nucleophile to react with activated MCPs via palladium catalysis.
View Article and Find Full Text PDFOrg Lett
November 2024
School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China.
In the presence of Wilkinson's catalyst, the -sulfinyl metalloenamines derived from NH-deprotonation of β,β-disubstituted enesulfinamides undergo nucleophilic allylic substitution with allyl carbonate, affording α-allylated ketimines with high stereoselectivity. These allylation products possess challenging acyclic quaternary stereocenters containing one allyl group and two alkyl groups that are both sterically and electronically similar (., Me and Et).
View Article and Find Full Text PDFChemistry
December 2024
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
The synthesis of α-tertiary amino acids (ATAAs), which are pivotal components in natural metabolism and pharmaceutical innovation, continues to attract significant research interest. Despite substantial advancements, the pursuit of a facile, versatile, and resource-efficient methodology remains an area of active development. In this work, we introduce a visible light-triggered three-component reaction involving readily available nitrosoarenes, N-acyl pyrazoles, and allyl or (bromomethyl)benzenes under mild conditions.
View Article and Find Full Text PDFChem Asian J
June 2024
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou Industrial Park, Suzhou, 215123, P. R. China.
We reported a chiral oxamide-phosphine ligand (COAP-Ph)-Pd-catalyzed asymmetric [3+2] cycloaddition reaction between vinyl cyclopropane compounds derived from 1,3-indanedione and 2-vinylcyclopropane-1,1-dicarboxylates with cyclic sulfonyl 1-azadienes. The corresponding reactions provided a series of enantiomerically active spiro cyclopentane-indandione and cyclopentane structures bearing three consecutive stereogenic centers in good yields with good diastereo- and enantioselectivity. The COAP-Pd complex serves not only to promote generation of chiral π-allyl-palladium intermediates and induce the asymmetry of the reaction, but also depress the background reaction.
View Article and Find Full Text PDF