A Dipolar Cyclization/Fragmentation Strategy for the Catalytic Asymmetric Synthesis of Chiral Eight-Membered Lactams

Zhang, Mao-Mao; Chen, Peng; Xiong, Wei; Hui, Xin-Shang; Lu, Liang-Qiu; Xiao, Wenjin

doi:10.31635/ccschem.021.202101476

Cited by 23 publications

(10 citation statements)

References 69 publications

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“…Chiral materials have drawn lots of attention due to their wide distribution in nature and organisms. [ 1–2 ] Their extremely asymmetric conformations, optical active features, and pharmacological properties make them promising candidates for various applications, such as chiral pharmaceutical, [ 3–4 ] enantioseparation, [ 5–7 ] asymmetric catalysis, [ 8–10 ] circularly polarized light source, [ 11–14 ] and photodetectors. [ 15–18 ] Traditional chiral compounds possess chiral carbon atoms/segments with point chirality, axial chirality, or helical conformation that do not have the mirror image.…”

Section: Introductionmentioning

confidence: 99%

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Stoichiometric and Chiral Stacking Tailoring of Dibenzocarbazole Analog–TCNB Charge‐Transfer Cocrystals via Supramolecular Assembly for Variable Optical Behaviors

Sun

Chen

et al. 2023

Advanced Optical Materials

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In this paper, three new donor–acceptor complex forms (zBC) containing a helical‐shape dibenzocarbazole analog (DBCz) as the electron donor and 1,2,4,5‐tetracyanobenzene (TCNB) as the electron acceptor via a simple solution‐processing strategy are reported. The beginning components self‐assembled into supramolecular frameworks with glamorous alignment modes and different molar ratios: ≈1:1 P or M‐enantiomer for α‐cocrystal, alternated P/M‐column stacking in mesmeric 2:3 β‐cocrystal, and segregated stacking of γ‐cocrystal. As a result, α‐cocrystal exhibits bright solid‐state red fluorescent, β‐cocrystal shows significant optical waveguide behavior with a low optical loss coefficient of ≈0.018 dB µm−1, and no visual light emission is observed for γ‐cocrystal under ultraviolet radiation. Interestingly, the α‐zBC crystal is not only emissive but also chiroptically active with dissymmetry factor (glum) of 0.004. This study on chiral stacking tailoring paves a way for functional design of organic charge‐transfer complex toward application in high‐performance organic optoelectronics.

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Section: Introductionmentioning

confidence: 99%

“…

asymmetric catalysis, [8][9][10] circularly polarized light source, [11][12][13][14] and photodetectors. [15][16][17][18] Traditional chiral compounds possess chiral carbon atoms/segments with point chirality, axial chirality, or helical conformation that do not have the mirror image.

…”

mentioning

confidence: 99%

Stoichiometric and Chiral Stacking Tailoring of Dibenzocarbazole Analog–TCNB Charge‐Transfer Cocrystals via Supramolecular Assembly for Variable Optical Behaviors

Sun

Chen

et al. 2023

Advanced Optical Materials

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“…Meanwhile, Xiao's group independently developed a threecomponent relay reaction for the generation of chiral 8membered lactams via asymmetric (4+4) cyclization (Scheme 7b). 20 The in situ generated Ir-activated dipole reacts with the cyclic nucleophilic dipolarophile 2-acylcyclobutanone, and then undergoes strain-release-driven fragmentation to form the desired eight-membered heterocycle 26.…”

Section: Allylation Relays Hemiketalization and Fragmentationmentioning

confidence: 99%

Asymmetric Allylic Substitution Reactions Based on Relay Catalysis

Feng,

Liu,

2024

Synthesis

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Transition-metal-catalyzed asymmetric allylic substitution reactions represent a hot research topic in the field of asymmetric synthesis, with significant progress having been made. Among diverse catalysis systems, relay catalysis enables sequential activation of multiple steps in one pot and the rapid construction of multiple chiral centers, providing a simple and powerful platform for organic synthesis. Recently, relay catalysis has been successfully applied to asymmetric allylic substitution reactions, and a variety of challenging transformations have been realized. This Short Review summarizes the related progress on asymmetric allylic substitution reactions based on relay catalysis over the last decade.1 Introduction2 The General Transformation Model3 Allylation Relays Further Reaction4 Initial Reaction Relays Allylation5 Conclusion and Outlook

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“…Very recently, Lu et al 56 and Yang, Tian and Deng et al 57 independently developed catalytic asymmetric (4+4) annulations of chiral Ir-containing 1,4-dipoles 92 with 2-acyl cyclobutanones 93 , which provided chiral 8-membered rings 94 with high yields and enantioselectivities (Scheme 20). Lu et al proposed a mechanism shown below.…”

Section: π-Allyl-m-type Mcrdsmentioning

confidence: 99%