Synthesis of Fused-Pyran Derivatives via a Base-Mediated Annulation of Bis-Allenoates Followed by Auto-Oxidation in Air

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(32), С. 6543 - 6549

Опубликована: Янв. 1, 2024

We introduce, for the first time, an inorganic base-mediated cyclization and auto-oxidation of bisallenones/bisalkynones. This reaction is realized under mild conditions through precise control base atmosphere, providing a wide range structurally diverse fused-pyran derivatives with moderate to excellent yields. Utilizing KOH as initiator nitrogen series novel cyclohexane-fused pyran was obtained primary product. In contrast, aerobic Na

Язык: Английский

---

Isochalcogenourea-Catalyzed Asymmetric (4+2)-Heterocycloadditions of Allenoates

Chemistry Letters, Год журнала: 2024, Номер 53(9)

Опубликована: Авг. 23, 2024

Abstract Allenoates are versatile reagents that can be used for numerous (formal) cycloaddition reactions under (chiral) Lewis base catalysis. Most commonly, the catalysts of choice phosphines, amines, and N-heterocyclic carbenes. We have recently established use readily available chiral isochalcogenoureas as asymmetric (4 + 2)-heterocycloadditions allenoates with various vinylogous acceptors. This represents a complementary approach allenoate activation gives access to highly functionalized dihydropyrans good excellent enantioselectivities diastereoselectivities.

Язык: Английский

---

Palladium-catalyzed four-component domino sulfonylation and carbonylation of 1,3-enynes at room temperature

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5851 - 5858

Опубликована: Янв. 1, 2024

A novel palladium-catalyzed four-component domino sulfonylation and carbonylation of 1,3-enynes has been developed, which enables the rapid incorporation allene, sulfone, carbonyl amine units into one single molecule simultaneously.

Язык: Английский

---

Regioselectivity Control in the Synthesis of Linear Conjugated Dienes Enabled by Manganese(I)-Catalyzed C–H Activation

ACS Catalysis, Год журнала: 2023, Номер 13(22), С. 14523 - 14529

Опубликована: Окт. 27, 2023

A highly selective Mn(I)-catalyzed dienylation of arenes and heteroarenes with acetylated allenes is described. The reported transformation proceeds by a simple one-pot procedure delivers linear 1,3-dienes as single products high stereoselectivity total regioselectivity. great variety allenic substrates bearing diverse substitution patterns can be applied in this protocol where the insertion step occurs at terminal carbon allene coupling partner, contrast former preparations dienes through C–H activation. This practical strategy features wide functional group tolerance preparative scale utility showing very good efficiency late-stage functionalization complex valuable molecules. Furthermore, synthetic importance method highlighted different derivatizations final products, which exhibit interesting fluorescence properties.

Язык: Английский

---

Chemical Fixation of CO2/CS2 to Access Iodoallenyl Oxazolidinones and Allenyl Thiazolidine-Thiones

Chemical Communications, Год журнала: 2024, Номер 60(66), С. 8756 - 8759

Опубликована: Янв. 1, 2024

Constructing heterocyclic compounds by chemical fixation of CO

Язык: Английский

---

Pd-Catalyzed Sequential Intramolecular Annulation/ Intermolecular [3+2] Cycloaddition of 5-Allenyloxazolidine-2,4-diones with Dipoles: Synthesis of Spiroheterocycles

Chemical Communications, Год журнала: 2024, Номер 60(76), С. 10516 - 10519

Опубликована: Янв. 1, 2024

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile

Язык: Английский

---

Regioselective Intermolecular Hydroamidation of β‐CF3‐1,3‐enynamides: An Approach to Tri‐substituted γ‐CF3‐allenamides

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(44)

Опубликована: Окт. 14, 2024

Abstract A simple base mediated, highly regioselective 1,4‐hydroamidation of β ‐CF 3 ‐1,3‐enynamides with secondary amides for synthesis tri‐substituted γ ‐allenamides compounds was developed. N ‐alkyl sulfonamides are generally good candidates the present transformation. could be employed potential value‐added such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2‐CF ‐putrescine derivatives.

Язык: Английский

---

Asymmetric isochalcogenourea-catalysed (4+2)-cycloadditions of ortho-quinone methides and allenoates

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 3, 2024

Chiral isochalcogenoureas catalyse the asymmetric (4 + 2)-cycloaddition of various allenoates with ortho -quinone methides giving access to chromane derivatives high selectivities.

Язык: Английский

---