HFIP in Organic Synthesis

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(15), P. 12544 - 12747

Published: July 17, 2022

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.

Language: Английский

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Spiroindoles as Intermediates/Products in Transition Metal-Catalyzed Dearomatization of Indoles

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(14), P. 9442 - 9475

Published: July 3, 2023

Spirocyclic indole derivatives are fascinating tridimensional molecular scaffolds from both a synthetic and biological point of view. Among the many strategies developed to access these structures, transition metal catalysis has recently led impressive advances, especially relying on unique reactivity dearomatized spirocyclic intermediates. These species can indeed evolve toward or nonspirocyclic products through rearomatization-driven processes, which at same time highly challenging control but also source large structural diversity. This review highlights most prominent methods past decade that involve spirocyclization tethered functional group may be activated by metal, leading rearomatized products. The discussion is particularly focused spiroindoleninium intermediate complex mechanistic features regarding its evolution, dependent catalytic systems.

Language: Английский

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Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(47), P. 6478 - 6510

Published: Sept. 8, 2021

Abstract Current medicinal chemistry relies heavily on the quality of building blocks, i. e. reagents used to introduce chemical diversity into target molecules. The last decade witnessed an emergence many novel (or well‐overlooked old) chemotypes for drug discovery, which is related adapting new synthetic methodologies, designing sp 3 ‐enriched bioisosteres, paying attention previously underrated even unwanted) structural motifs, or combination thereof. In this review with 532 references, a survey selected that emerged recently in provided, focus synthesis corresponding blocks. Thus, saturated (hetero)aliphatic boronates, sulfonyl fluorides, sulfinates, non‐classical benzene isosteres, bicyclic morpholine/piperidine/piperazine analogs, as well gem ‐difluorinated cycloalkanes (as example emerging fluorinated motifs) are discussed.

Language: Английский

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Catalytic asymmetric preparation of pyrroloindolines: strategies and applications to total synthesis

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(10), P. 5985 - 6012

Published: Jan. 1, 2021

Pyrroloindolines are widely present in natural products. In this review, we summarize state-of-the-art of catalytic asymmetric synthesis pyrroloindolines, as well related applications to products total synthesis.

Language: Английский

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How far have we explored fungi to fight cancer?

Seminars in Cancer Biology, Journal Year: 2021, Volume and Issue: 86, P. 976 - 989

Published: March 18, 2021

Language: Английский

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Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(21), P. 11524 - 11529

Published: May 18, 2023

A method for C(sp

Language: Английский

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Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry

Chemical Science, Journal Year: 2020, Volume and Issue: 11(30), P. 7807 - 7812

Published: Jan. 1, 2020

A general, practical, and efficient synthesis of N,N′-disubstituted sulfamides has been developed applied to the preparation polysulfamides, a virtually unknown class polymers.

Language: Английский

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Recent advances in the total synthesis of natural products bearing the contiguous all-carbon quaternary stereocenters

Tetrahedron Letters, Journal Year: 2021, Volume and Issue: 71, P. 153029 - 153029

Published: March 27, 2021

Language: Английский

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The Transformative Power of Biocatalysis in Convergent Synthesis

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(12), P. 5214 - 5225

Published: March 15, 2022

Achieving convergent synthetic strategies has long been a gold standard in constructing complex molecular skeletons, allowing for the rapid generation of complexity comparatively streamlined routes. Traditionally, biocatalysis not played prominent role laboratory synthesis, with application biocatalysts primarily limited to synthesis chiral fragments. Although use enzymes enable approaches is relatively new and emerging, combining efficiency transformations selectivity achievable through creates opportunities efficient strategies. This Perspective provides an overview recent developments biocatalytic offers insights into advantages these methods compared their small molecule-based counterparts.

Language: Английский

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Mitsunobu Reaction: A Powerful Tool for the Synthesis of Natural Products: A Review

Molecules, Journal Year: 2022, Volume and Issue: 27(20), P. 6953 - 6953

Published: Oct. 17, 2022

The Mitsunobu reaction plays a vital part in organic chemistry due to its wide synthetic applications. It is considered as significant for the interconversion of one functional group (alcohol) another (ester) presence oxidizing agents (azodicarboxylates) and reducing (phosphines). renowned stereoselective which inverts stereochemical configuration end products. One most important applications role synthesis natural This review article will focus on contribution towards total products, highlighting their biological potential during recent years.

Language: Английский

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