Ruthenium-Catalyzed Cyclic Carbonylation of Allenyl Alcohols. Selective Synthesis of γ- and δ-Lactones

Yoneda, Eiji; Kaneko, Takuya; Zhang, Shiwei; Onitsuka, Kiyotaka; Takahashi, Shigetoshi

doi:10.1021/ol990377d

Cited by 114 publications

(33 citation statements)

References 27 publications

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“…Recently, allenols have been proven as versatile building blocks in organic synthesis 5,[50][51][52][53] . By applying this protocol, acetate-protected trisubstituted a-and b-allenols could be obtained in moderate to good yields (Fig.…”

Section: Resultsmentioning

confidence: 99%

Cadmium iodide-mediated allenylation of terminal alkynes with ketones

et al. 2013

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Allenes are important building blocks in organic synthesis and have attracted much attention from researchers worldwide. So far, mono-and 1,3-disubstituted allenes can be prepared easily by applying the allenylation of terminal alkynes reaction of aldehydes. However, trisubstituted allenes have never been reported using this reaction due to the extremely low reactivity of ketones. Here, we report the one-pot synthesis of trisubstituted allenes from terminal alkynes and ketones utilizing cadmium iodide as the mediator. With this protocol, a series of different allenes, including 1,5-bisallenes and optically active allenols, which are especially important in synthetic chemistry, have been successfully prepared.

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Section: Resultsmentioning

confidence: 99%

Cadmium iodide-mediated allenylation of terminal alkynes with ketones

et al. 2013

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“…Cyclocarbonylation of 3,4-pentadien-1-ol and 2-methyl-4,5-hexadien-2-ol, in the presence of Ru3(CO)12/Et3N as a catalytic system, produced in the same way 5,6-dihydro-3-methyl-2H-pyran-2-one and 5,6-dihydro-6,6-dimethyl-3-methyl-2H-pyran-2-one δ-lactones, respectively, in high yields (Scheme 17) [28].…”

Section: Brief Overview On the Functional Groups Involved And Proposementioning

confidence: 93%

“…Proton attack from X and metal elimination affords cyclic carbonyl compounds D [see refs. 24,28,33,39,72,89].…”

Section: Brief Overview On the Functional Groups Involved And Proposementioning

confidence: 99%

Synthesis of Heterocycles by Transition Metals-Catalyzed Cyclocarbonylation Reactions

Vasapollo

Mele

2006

COC

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The synthesis of heterocyclic compounds such as lactones, lactams, pyrrolidinones and others can be achieved by cyclocarbonylation reactions catalyzed by transition metal complexes. The combination of palladium salts with certain different ligands turned out to be the most efficient catalyst systems to accomplish such cyclocarbonylation reactions. New synthetic strategies and novel approaches devoted to the preparation of such compounds having different ring size still remain a stimulating area of academic and industrial research.

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“…In this case, an alternative hydropalladation mechanism is proposed, since a syn-carbopalladation would result in a highly strained 6-membered lactone with a trans double bond [31]. The corresponding reaction of allenes was only realized recently with catalytic Ru 3 (CO) 12 yielding five and six membered a,b-unsaturated lactones [32].…”

Section: Hydrocarbonylation Of C¼c and CC Bondsmentioning

confidence: 99%