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• W2080176699 abstract "Palladium(0)-catalyzed reaction of allene-substituted allylic carboxylates 3−8 employing 2−5 mol % of Pd(dba)2 in refluxing toluene leads to the carbocyclization and elimination of carboxylic acid to give bicyclo[4.3.0]nonadiene and bicyclo[5.3.0]decadiene derivatives (12−17). The carbon−carbon bond formation is stereospecific, occurring syn with respect to the leaving group. Addition of maleic anhydride as a ligand to the above-mentioned procedures changed the outcome of the reaction, and under these conditions 3−5 afforded cycloisomerized products 21−23. The experimental results are consistent with a mechanism involving oxidative addition of the allylic carboxylate to Pd(0) to give an electron-deficient (π-allyl)palladium intermediate, followed by nucleophilic attack by the allene on the face of the π-allyl opposite to that of the palladium atom. Furthermore, it was found that the Pd(dba)2-catalyzed cyclization of the trans-cycloheptene derivative (trans-8) can be directed to give either the trans-fused (trans-17) or the cis-fused (cis-17) ring system by altering the solvent. The former reaction proceeds via a nucleophilic trans-allene attack on the (π-allyl)palladium intermediate, whereas the latter involves a syn-allene insertion into the allyl−Pd bond of the same intermediate. The products from the carbocylization undergo stereoselective Diels−Alder reactions to give stereodefined polycyclic systems in high yields." @default.
• W2080176699 created "2016-06-24" @default.
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• W2080176699 date "2003-10-23" @default.
• W2080176699 modified "2023-09-27" @default.
• W2080176699 title "Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates" @default.
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• W2080176699 doi "https://doi.org/10.1021/ja037398u" @default.
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