Stereodivergent Macrocyclization in Dynamic Chiral Confinement DOI Open Access

Linfeng Tan,

Tianyi Zheng, Yongsheng Li

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 18, 2024

The absolute and relative configurations of a macrocyclic natural product bearing multiple chirality have crucial influence on its physical biological properties. Nevertheless, their preparation with full stereocontrol remains largely unexplored in synthetic community. Here, we show stereodivergent macrocyclization under dynamic chiral confinement which the stepwise switching space directs complete stereocontrol. To confine substrate space, used capsule enclosing is collectively switchable response to external stimuli, but conformations are firmly fixed by subsequent self-assembly. consecutive enables confined reactions an enclosed achiral sequentially install diverse macrocycle single pot operation, thus changing only sequence stimuli access remarkable stereodivergence process.

Язык: Английский

Chemistry for Water Treatment under Nanoconfinement DOI
Wanyi Fu, Ziyao Liu, Dan Li

и другие.

Water Research, Год журнала: 2025, Номер 275, С. 123173 - 123173

Опубликована: Янв. 21, 2025

Язык: Английский

Процитировано

2
Complete Computational Reaction Mechanism for Foldamer-Catalyzed Aldol Condensation DOI

Reilly Osadchey Brown,

Darren Demapan,

Qiang Cui

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(10), С. 7624 - 7638

Опубликована: Май 1, 2024

Foldamers, small synthetic peptides made of

Язык: Английский

Процитировано

3
Supramolecular Synthesis of Star Polymers DOI Creative Commons
Takeharu Haino, Natsumi Nitta

ChemPlusChem, Год журнала: 2024, Номер 89(5)

Опубликована: Фев. 26, 2024

Supramolecular polymers, in which monomers are assembled via intermolecular interactions, have been extensively studied. The fusion of supramolecular polymers with conventional has attracted the attention many researchers. In this review article, recent progress construction star including regular and miktoarm is discussed. initial sections briefly provide an overview classification synthesis methods for polymers. Coordination-driven self-assembly was investigated Star multiple polymer chains radiating from metal-organic polyhedra (MOPs) also described. Particular focus placed on featuring cores formed through hydrogen-bonding-directed self-assembly. After describing based host-guest complexes, molecular recognition coordination capsules detailed.

Язык: Английский

Процитировано

3
Supramolecular Handshakes: Characterization of Urea‐Carboxylate Interactions Within Calixarene Frameworks DOI
Marija Cvetnić, Nikola Cindro, Edi Topić

и другие.

ChemPlusChem, Год журнала: 2024, Номер 89(7)

Опубликована: Март 25, 2024

Abstract The research of molecular capsules offers high application potential and numerous benefits in various fields. With the aim forming supramolecular which can be reversibly assembled dissociated by simple external stimuli, we studied interactions between calixarenes containing urea carboxylate moieties. To this end two ureido‐derivatives p ‐ tert ‐butylcalix[4]arene comprising phenylureido‐moieties diacetate‐calix[4]arenes were prepared. binding acetate calixarene acetonitrile was characterized, revealing affinity ureido‐calixarenes for carboxylates. This suggested uniting complementary calix[4]arenes via H‐bonds carboxylic groups assembly examined detail means UV, 1 H NMR, ITC, DOSY, MS, conductometry providing insight structure‐stability relationship. tetraureido‐calixarene derivative formed most stable heterodimers with featuring practically quantitative association upon mixing counterparts. possibility controlling formation heterodimer protonating carboxylates, thereby hindering critical capsule assembly, investigated. Indeed, reversibility breaking re‐forming addition an acid base to solution urea‐ carboxylate‐derivative calix[4]arene demonstrated using NMR spectroscopy.

Язык: Английский

Процитировано

1
Exploring a Non-Comfort Zone: Central Chirality-Generating Macrocyclizations DOI
Kuan Zheng, Ran Hong

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7355 - 7365

Опубликована: Май 10, 2024

Macrocyclization reactions that are capable of stereoselectively co-creating one or more stereogenic centers have become useful strategies for the effective syntheses structurally and functionally diverse organic molecules. This JOCSynopsis summarizes recent progress in field natural product analogue syntheses, including both bioinspired non-bioinspired macrocyclic disconnections. Selected examples organized on basis sources asymmetric inductions.

Язык: Английский

Процитировано

1
Catalyzing the Enantioselective Tail‐to‐Head Terpene Cyclization inside Optically Active Hexameric Resorcin[4]arene Capsules: A Surprising Odd‐Even Effect of the Catalyst DOI Creative Commons

Giacomo Persiani,

Daria Sokolova, Roman Ivanov

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 15, 2024

Abstract Terpenes, created in Nature via tail‐to‐head terpene (THT) cyclizations, have long fascinated chemists due to their complex structures and biological activities. Recreating such THT cyclizations the laboratory using man‐made catalysts has been challenging. Especially difficult is performing reaction an enantioselective fashion, as substrate flexible does not contain much functionality form strong interactions with chiral catalyst. This study explores cyclization inside hexameric capsules self‐assembled from optically active resorcin[4]arene derivatives. An unexpected odd‐even effect, where enantioselectivity of depended on length alkyl chain attached capsule was uncovered. To our knowledge, this first example effect catalyst itself, also instance which related reaction.

Язык: Английский

Процитировано

1
Active Molecular Gripper as a Macrocycle Synthesizer DOI
Tianyi Zheng,

Linfeng Tan,

Minhyeok Lee

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(37), С. 25451 - 25455

Опубликована: Сен. 3, 2024

A confined space preorganizes substrates, which substantially changes their chemical reactivity and selectivity; however, the performance as a reaction vessel is hampered by insensitivity to environmental changes. Here, we show dynamic formed substrate grasping of an amphiphilic host with branched aromatic arms active molecular gripper capable performing grasping, macrocyclization, product release acting macrocycle synthesizer. The gripper, further stabilized gel formation. Confining linear in closed form triggers spontaneous ring-forming opening. consecutive open-closed switching enables repetitive tasks be performed remarkable working efficiency.

Язык: Английский

Процитировано

0
Stereodivergent Macrocyclization in Dynamic Chiral Confinement DOI Open Access

Linfeng Tan,

Tianyi Zheng, Yongsheng Li

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 18, 2024

The absolute and relative configurations of a macrocyclic natural product bearing multiple chirality have crucial influence on its physical biological properties. Nevertheless, their preparation with full stereocontrol remains largely unexplored in synthetic community. Here, we show stereodivergent macrocyclization under dynamic chiral confinement which the stepwise switching space directs complete stereocontrol. To confine substrate space, used capsule enclosing is collectively switchable response to external stimuli, but conformations are firmly fixed by subsequent self-assembly. consecutive enables confined reactions an enclosed achiral sequentially install diverse macrocycle single pot operation, thus changing only sequence stimuli access remarkable stereodivergence process.

Язык: Английский

Процитировано

0