Palladium-catalyzed decarboxylative cyclization of α-acyloxyketones having an allene moiety in the tether

Yabuta, Akimasa; Oonishi, Yoshihiro; Doi, Ryohei; Morisaki, Kazuhiro; Sato, Yoshihiro

doi:10.1039/d2nj04657a

Cited by 1 publication

(2 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[179] In a different contribution, the cyclohexene motif has been generated in cyclohexenones 370 through a palladium-catalyzed decarboxylative cyclization of γ-allenones 369 (Scheme 66b). [180] The reaction of 1,2-allenyl ketones and vinyl ketones with or without the intervention of a second nucleophile, has provided a quick route to build saturated or partially unsaturated cyclic structures. Thus, α-allenones 2 react with vinyl ketones 372 to build cyclohexanones 373, cyclohexenones 374 and cyclohexadienones 376 through related mechanistic pathways (Scheme 67).…”

Section: Synthesis Of Cycloalkanes and Cycloalkenesmentioning

confidence: 99%

“…Then, benzopyrylium formation and [4+2] cycloaddition with the participation of the terminal allenic double bond and the diene moiety of 367 conduct to bridged polycycles 368 , which finally have provided fused polycycles 365 after decarboxylation (Scheme 66a) [179] . In a different contribution, the cyclohexene motif has been generated in cyclohexenones 370 through a palladium‐catalyzed decarboxylative cyclization of γ‐allenones 369 (Scheme 66b) [180] …”

Section: Synthetic Utilitymentioning

confidence: 99%

See 1 more Smart Citation

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

View full text Add to dashboard Cite

Conjugated and non-conjugated allenones appear as recurring motifs in organic synthesis, natural products and mechanistic investigations showing unique properties and applications. The ability of allenones to build cycles has provided a direct access to strained systems, medium-sized rings, arenes, heterocycles and complex polycycles. In addition, allenones have served as models in mechanistic investigations and catalysis. The critic compilation herein presented will provide an exhaustive overview of the synthetic possibilities allenones may offer, which certainly will inspire our community in their search of more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and improve our knowledge in theoretical organic chemistry. Great part of this review will discuss synthetic aspects, catalysis innovation and mechanistic insights of the chemical transformations implying the allenone motif. In addition, many examples on total synthesis and pharmacologically active compounds will be described. We hope that this overview will be attractive to the organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products and medicinal chemistry communities. 3.5. Synthesis of Spirocycles and Bridged Structures 3.6. Open-Chain Structures from Allenones 3.7. Allenones in Total Synthesis 4.

show abstract

Section: Synthesis Of Cycloalkanes and Cycloalkenesmentioning

confidence: 99%