Organoboron Compounds Towards Asymmetric Pericyclic Reaction; Exploitation to Bioactive Molecule Synthesis

Reactions of an Aluminium(I) Reagent with 1,2-, 1,3- and 1,5-Dienes: Dearomatisation, Reversibility, and a Pericyclic Mechanism

10.26434/chemrxiv.11400171.v1 ◽

2019 ◽

Author(s):

Clare Bakewell ◽

Martí Garçon ◽

Richard Y Kong ◽

Louisa O'Hare ◽

Andrew J. P. White ◽

...

Keyword(s):

Reaction Mechanism ◽

Dft Calculations ◽

Transition State ◽

Reaction Pathways ◽

Aromatic Rings ◽

Aromatic Character ◽

Pericyclic Reaction

The reactions of an aluminium(I) reagent with a series of 1,2-, 1,3- and 1,5-dienes are reported. In the case of 1,3-dienes the reaction occurs by a pericyclic reaction mechanism, specifically a cheletropic cycloaddition, to form aluminocyclopentene containing products. This mechanism has been interrogated by stereochemical experiments and DFT calculations. The stereochemical experiments show that the (4+1) cycloaddition follows a suprafacial topology, while calculations support a concerted albeit asynchronous pathway in which the transition state demonstrates aromatic character. Remarkably, the substrate scope of the (4+1) cycloaddition includes dienes that are either in part, or entirely, contained within aromatic rings. In these cases, reactions occur with dearomatisation of the substrate and can be reversible. In the case of 1,2- or 1,5-dienes complementary reactivity is observed; the orthogonal nature of the C=C π-bonds (1,2-diene) and the homoconjugated system (1,5-diene) both disfavour a (4+1) cycloaddition. Rather, reaction pathways are determined by an initial (2+1) cycloaddition to form an aluminocyclopropane intermediate which can in turn undergo insertion of a further C=C π-bond leading to complex organometallic products that incorporate fused hydrocarbon rings.

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Faculty Opinions recommendation of The pyridine ring of NAD is formed by a nonenzymatic pericyclic reaction.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1024025.292978 ◽

2005 ◽

Author(s):

Mark Nelson

Keyword(s):

Pyridine Ring ◽

Pericyclic Reaction

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Ethanolamine: A Potential Promoiety with Additional Effects in the Brain

CNS & Neurological Disorders - Drug Targets ◽

10.2174/1871527319999201211204645 ◽

2020 ◽

Vol 19 ◽

Author(s):

Asfree Gwanyanya ◽

Christie Nicole Godsmark ◽

Roisin Kelly-Laubscher

Keyword(s):

Central Nervous System ◽

Nervous System ◽

Drug Design ◽

Cell Signaling ◽

Blood Brain Barrier ◽

Brain Barrier ◽

The Central Nervous System ◽

Bioactive Molecule ◽

Positive Functions ◽

The Brain

Abstract: Ethanolamine is a bioactive molecule found in several cells, including those in the central nervous system (CNS). In the brain, ethanolamine and ethanolamine-related molecules have emerged as prodrug moieties that can promote drug movement across the blood-brain barrier. This improvement in the ability to target drugs to the brain may also mean that in the process ethanolamine concentrations in the brain are increased enough for ethanolamine to exert its own neurological ac-tions. Ethanolamine and its associated products have various positive functions ranging from cell signaling to molecular storage, and alterations in their levels have been linked to neurodegenerative conditions such as Alzheimer’s disease. This mini-review focuses on the effects of ethanolamine in the CNS and highlights the possible implications of these effects for drug design.

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Chan–Lam-Type C–S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

Organic Letters ◽

10.1021/acs.orglett.1c02299 ◽

2021 ◽

Author(s):

Long Yin Lam ◽

Cong Ma

Keyword(s):

Coupling Reaction ◽

Organoboron Compounds ◽

Type C

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Transition-metal catalyzed carboxylation of organoboron compounds with CO2

Journal of CO2 Utilization ◽

10.1016/j.jcou.2020.101403 ◽

2021 ◽

Vol 45 ◽

pp. 101403

Author(s):

Wei Xu ◽

Danjun Guo ◽

Abdol Ghaffar Ebadi ◽

Mohsen Toughani ◽

Esmail Vessally

Keyword(s):

Transition Metal ◽

Organoboron Compounds ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Perspective of Organoboron Chemistry

Synlett ◽

10.1055/a-1405-7012 ◽

2021 ◽

Author(s):

Lingbing Kong ◽

Chunming Cui

Keyword(s):

Recent Progress ◽

Main Group ◽

Future Research ◽

Materials Chemistry ◽

Organoboron Compounds ◽

The Future ◽

Research Hotspots

Organoboron compounds play prominent roles in structural, synthetic and materials chemistry because the boron atoms may feature electrophilic, amphiphilic and nucleophilic characters. This perspective briefly describes the most recent progress in organoboron chemistry by focusing on both new advent boron molecules and their applications, which greatly inspire the interest of main group chemists. Meanwhile, the future research hotspots based on these pioneering results are also discussed.

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