Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(3), P. 1003 - 1003

Published: Jan. 1, 2025

Language: Английский

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Assembly of 3-Halooxindoles via Interrupted Semipinacol Rearrangement: Enabling Concise Total Synthesis of CPC-1

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134672 - 134672

Published: April 1, 2025

Language: Английский

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Catalytic Asymmetric Synthesis of Vicinal Quaternary Stereocenters Enabled by Alkylation of α,α-Disubstituted Aldehydes with 3-Bromooxindoles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3086 - 3090

Published: April 9, 2024

An organocatalytic enantioselective alkylation of α,α-disubstituted aldehydes with 3-bromooxindoles is reported. Enantioenriched oxindoles vicinal quaternary stereocenters are accessed by an asymmetric conjugate addition process branched o-azaxylylene intermediates (indol-2-ones). Key to the success highly diastereo- and transformations combined use a triphenylsilyl-protected β-amino alcohol catalyst derived from spiropyrrolidine scaffold 3,5-dinitrobenzoic acid. This study also presents rare example aldehyde formation consecutive stereocenters.

Language: Английский

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Construction of Acyclic Quaternary Carbon Stereocenters via Enantioselective Nickel Catalysis^†

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(20), P. 2485 - 2498

Published: June 21, 2024

Comprehensive Summary The construction of acyclic quaternary carbon stereocenters, which are ubiquitous in many bioactive compounds, pharmaceuticals and natural products, has been a long persuit synthetic organic chemistry. Among numerous methods, enantioselective nickel‐catalysis attracted incremental attention recent years. This review summarizes the development asymmetric strategies, research progress, mechanistic investigations for generation stereocenters via nickel catalysis. Key Scientists In 2006, Zhou group RajanBabu realized nickel‐catalyzed hydrovinylation α‐substituted styrenes ethylene to construct (QCSs) by using spiro‐ binaphthyl phosphoramidite ligands, respectively. 2016, Watson developed Suzuki‐Miyaura arylation generate QCSs chirality transfer reaction. 2017, Feng Fu conjugated/Michael additions build QCSs, 2020, Fang made first success hydrocyanation alkenes allenes. 2021, Gregory C. co‐workers disclosed α‐functionalization carbonyl compounds that could form QCSs. At same time, Shi constructed chiral functionalization alkenes. 2023, Kleij applied new strategy Ni‐catalyzed regio‐ homoallylic coupling year, Tao demonstrated novel is dinickel‐catalyzed α‐alkylation with alkyl iodides.

Language: Английский

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New Synthetic Approaches for the Construction of Enantioenriched Molecules Bearing Quaternary Stereocenters

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4294 - 4322

Published: Aug. 17, 2024

Abstract Optically active molecule architectures stand as an important class of organic compounds and occupy a key role in academic industrial communities. Particularly, the molecules bearing quaternary carbon are vital importance because its favorable conformation valuable three‐dimensional molecules, which frequently play broad spectrum functional materials, pharmaceutical relevant natural agrochemicals. Over past few decades, large number synthetic strategies for enantioselective construction with chiral centers have been focus research initiatives. In this review, state‐of‐the‐art toward synthesis enantioenriched stereocenters summarized, could be segmented into four categories: 1) Construction optically by addition to prochiral sp 2 carbon; 2) all‐carbon via substitution at non‐chiral tetra‐substituted 3) kinetic resolution; 4) desymmetrization reactions.

Language: Английский

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Allylsilanes, Allyltins, and Related Compounds

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

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