Enantioselective Synthesis of Spiro Heterocyclic Compounds Using a Combination of Organocatalysis and Transition‐Metal Catalysis

The Chemical Record, Год журнала: 2023, Номер 23(7)

Опубликована: Янв. 26, 2023

Abstract Over the last ten years, combination of organocatalysis with transition metal (TM) catalysis has become one most important toolboxes used for synthesizing optically pure compounds containing chiral quaternary centers, including spiro heterocyclic molecules. The dominant method in enantioselective synthesis based on synergistic includes aminocatalysis and NHC catalysis, as already established covalent organocatalytic strategies. Another area widely combined TM producing enantiomerically enriched is non‐covalent dominated by phosphoric acids, thiourea, squaramide derivatives. This review article aims to summarize methods constructing spirocyclic heterocycles a catalysis.

Язык: Английский

---

Phosphine-catalyzed [5+1] annulation of β′-acetoxy allenoates: straightforward access to tetrahydroquinoline derivatives

Chemical Communications, Год журнала: 2023, Номер 59(78), С. 11712 - 11715

Опубликована: Янв. 1, 2023

An unprecedented phosphine-catalyzed [5+1] annulation of β'-acetoxy allenoates with 1,5-dinucleophiles has been developed, which provides novel and facile access to functionalized tetrahydroquinolines in good high yields the presence PPh3 K3PO4 under mild reaction conditions. Notably, it is first report acting as C1 synthons Lewis base-catalyzed reactions.

Язык: Английский

---

Construction of spirotetrahydroquinolines fused with medium-sized rings via TBHP/base-promoted spirocyclization reactions

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An efficient and straightforward methodology for the synthesis of spirotetrahydroquinolines fused with medium-sized rings (including 7, 8, 9-membered rings) by TBHP/base-promoted spirocyclization reactions has been developed.

Язык: Английский

---

Remote stereocontrol in the (4 + 2) cycloadditions of 1,7-zwitterions: Asymmetric synthesis of multifunctionalized tetrahydroquinoline derivatives

Chinese Chemical Letters, Год журнала: 2023, Номер 35(1), С. 108295 - 108295

Опубликована: Март 5, 2023

Язык: Английский

---

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons

Chemical Synthesis, Год журнала: 2023, Номер 3(1), С. 7 - 7

Опубликована: Янв. 1, 2023

Chiral spirolactones, including spiropropyllactones, spirobutyrolactones, and spirovalerolactones, are important heterocyclic frameworks that attracted the attention of organic medicinal chemists because these motifs constitute core structure several natural products bioactive molecules. The absolute configuration substituents on fully substituted spirocyclic stereocenter lactone can potentially enhance specificity for ligand-protein binding bioavailability, potency, metabolic stability. So, intensive from has been paid to synthetic methods leading such prominent structural motifs. be divided into two main classes. first approach takes advantage presence existing focuses its functionalization. second is framework constructed various precursors in a direct spirolactonization reaction. In this review, convenience reading, recent advances synthesis spirolactones summarized discussed according major organocatalytic asymmetric routes: (i) using lactone-related as building blocks; (ii) reaction reagents. This review also describes both mechanisms related transformations, gives some insights challenging issues research field, which will enlighten future development field.

Язык: Английский

---

Enantioselective Synthesis of Dispirooxindole Derivatives via Asymmetric Catalytic Cascade Reactions

Synthesis, Год журнала: 2023, Номер 55(12), С. 1929 - 1939

Опубликована: Янв. 22, 2023

Abstract A series of optically active 3,3′-pyrrolidinyl-dispirooxindole derivatives containing a CF3 moiety have been efficiently constructed through asymmetric catalytic cascade reactions catalyzed by cinchona-derived bifunctional squaramide catalyst, bearing four contiguous stereogenic centers, two which are vicinal spiro-stereocenters. Additionally, wide range substituted products were achieved with moderate to high yields (up 99% yield) and excellent stereoselectivities >20:1 dr for all cases up ee).

Язык: Английский

---

Cu+-Based Composite Metal Oxides Enable the Efficient [4 + 2] Annulation Reactions between Tertiary Anilines and Tetrahydrofuran

Опубликована: Янв. 1, 2023

An efficient heterogeneous catalytic system for the [4+2] annulation reactions between tertiary anilines and tetrahydrofuran has been developed based on CuCoFe layered double oxide in study. Cu+ species was believed to play crucial role transformation, synergistic effect Cu CoFe observed reaction. Various could be tolerated by present system. A series of control experiments were conducted determine reaction intermediates. distinctive mechanism described these results kinetic isotopic effects experiments.

Язык: Английский

---

Six-membered ring systems: pyridines and benzo derivatives

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 383 - 425

Опубликована: Янв. 1, 2023

Язык: Английский

---

Design, synthesis and evaluation of structurally diverse polycyclic harmaline scaffolds as anticancer agents

New Journal of Chemistry, Год журнала: 2024, Номер 48(14), С. 6322 - 6334

Опубликована: Янв. 1, 2024

This is the first example of harmaline scaffolds as acceptor/acceptor-based N–C–C synthons and evaluation 3at an anticancer agent.

Язык: Английский

---

Enantioselective Construction of Polycyclic Chromanes through Organocatalytic Sequential Quintuple Reaction via One‐Pot Step‐Wise Procedure

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(18), С. 2197 - 2202

Опубликована: Май 14, 2024

Comprehensive Summary An efficient and highly stereoselective synthetic method to access polycyclic chromanes has been achieved through organocatalyzed one‐pot step‐wise reactions involving 2‐hydroxycinnamaldehydes, 2‐aminochalcones, malononitrile as substrates. The underwent a quintuple process by aza‐Michael/Michael/Knoevenagel/oxa‐Michael/aldol‐type reaction in sequence give products bearing 3 new generated rings 5 chiral centers moderate quantitative yields with excellent stereoselectivities. A novel retro‐reaction mechanism was discovered the transformations of products.

Язык: Английский

---