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Total syntheses of the parvistemoline alkaloids enabled by stereocontrolled Ir/Pd-catalyzed allylic alkylation.
Nat Commun
December 2024
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.
The functionalized polycycle with densely contiguous tertiary stereocenters is a formidable challenge in synthesizing the parvistemoline family of Stemona alkaloids. We herein report their catalytic, asymmetric total syntheses in 13-14 steps from commercially available 2-(methoxycarbonyl)-pyrrole, featuring the development and deployment of an Ir/Pd-synergistically-catalyzed allylation of α-non-substituted keto esters with secondary aryl-substituted alcohols, stereodivergently accessible to four stereoisomers. Using chiral Pd-enolate and Ir π-allyl complex under neutral conditions, no epimerization occurs.
View Article and Find Full Text PDFAsymmetric cyclopropanation an electro-organocatalytic cascade.
Chem Commun (Camb)
November 2024
Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia.
We report an iminium ion-promoted, asymmetric synthesis of cyclopropanes an electrocatalytic, iodine-mediated ring closure. The mild, controlled electrochemical generation of electrophilic iodine species in catalytic quantities prevents organocatalyst deactivation, while also eliminating the need for halogenating reagents, thus simplifying traditional synthetic approaches.
View Article and Find Full Text PDFMulticomponent Construction of Tertiary Alkylamines by Photoredox/Nickel-Catalyzed Aminoalkylation of Organohalides.
J Am Chem Soc
October 2024
Department of Chemistry, National University of Singapore, 4 Science Drive 2, Singapore 117544, Republic of Singapore.
Article Synopsis
- * The study presents a novel method using dual photoredox/nickel catalysis to create tertiary alkylamines from organohalides and secondary alkylamines, via α-amino radicals and iminium ions.
- * This approach also allows for complex four-component reactions and can produce enantioenriched compounds, providing a promising route for synthesizing diverse tertiary amines.
Synthesis, crystal structure, and Hirshfeld surface analysis of 1,3-di-hydro-2-benzimidazol-2-iminium 3-carb-oxy-4-hy-droxy-benzene-sulfonate.
Acta Crystallogr E Crystallogr Commun
September 2024
Uzbekistan Japan Innovation Center of Youth, University str. 2B, Tashkent, 100095, Uzbekistan.
The asymmetric unit of the title salt, CHN ·CHOS, comprises two 1,3-di-hydro-2-benzimidazol-2-iminium cations and two 2-hy-droxy-5-sulfobenzoate anions (' = 2). In the crystal, the mol-ecules inter-act through N-H⋯O, O-H⋯O hydrogen bonds and C-O⋯π contacts. The hydrogen-bonding inter-actions lead to the formation of layers parallel to (01).
View Article and Find Full Text PDFDeciphering Asymmetric Brønsted Base-Aminocatalytic Mode in Pudovik/[1,2]-Phospha-Brook Rearrangement/Michael Cascade Reaction.
J Org Chem
October 2024
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
An approach involving the use of a bifunctional aminocatalyst containing Brønsted base and iminium activation sites for asymmetric multicomponent reactions involving [1,2]-phospha-Brook rearrangement has yet to be realized. Herein, we present an aminocatalytic enantioselective conjugate addition of α-phosphonyloxy enolates formed [1,2]-phospha-Brook rearrangement to α,β-unsaturated ketones. The methodology unfolds a simple one-pot operation consisting of a robust additive-free catalytic system providing a series of oxindole derivatives having two contiguous stereocenters in high yields with excellent stereoselectivities.
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