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284 When the reaction was carried out using P(o-tolyl)3 as a ligand, the carbapenam 671 was obtained in 57% yield, while the reaction of 670 using DPPF gave the carbacepham 672 in 56% yield. A novel synthetic method for the cyclic carbonates 675 was reported by Ihara et al. 285 The reaction of the 4-methoxycarbonyloxy-2-butyn-1-ol 673a with phenols 674 in the presence of Pd2(dba)3‚ CHCl3 and dppe gave 675 in good yields. The allenylpalladium 676 is attacked by ArOH 674 to produce the π-allylpalladium complex 677, which undergoes insertion of CO2 to give 675.

291 Doyle et al. 290d Davies et al. 291d The reaction proceeds through cyclopropanation and subsequent Cope rearrangement from 695 to 694. 292e The reaction of 698 in the presence of Rh2(OAc)4 in hexane gave the furan 699 in 98% yield, while the reaction of 698 using CH2Cl2 as a solvent produced the azetidinone 700 (Scheme 217). The reaction producing 699 proceeds through the rhodium vinyl carbenoid 701, and subsequent 6-π cyclization gives 699. The azetidinone Scheme 217 Scheme 218. Intramolecular Reaction of Diazo Compounds Bearing a Heteroatom-Hydrogen Bond 700 is afforded by the C-H insertion into a methyl group of 698.

The insertion of CO into the C-Pd bond of 313, followed by methanolysis of the resulting acylpalladium complex, affords the esters 312 and Pd(0) catalyst. The Pd(0) is oxidized to Pd(II) by molecular oxygen, and thus the catalytic cycle operates well. 167 The introduction of an o-methoxy group on the benzene ring of the alkynyl substituent increased the yields of the cyclization products. The reaction proceeds through the nucleophilic attack of the nitrogen atom on electron-deficient alkyne 317, the formation of the alkenylpalladium intermediate 318, the insertion of the alkenes 315 into the C-Pd bond 319, and β-hydride elimination.

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