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Entry l 3 o Diene = Ester Product Yielda) CH3COOEt 91 CH3(CH2)2COOEt 96 PhCOOEt 55 = a< CH3(CH2)2COOEt a) Fused bicyclic product was obtained under reflux. 59 74 16 I Rieke Metals: Highly Reactive Metal Powders Table 1-6. Reactions of diene-magnesium reagents with carboxylic esters. Formation of ketones. Entry Diene Ester Product /3. y-unsaturated Yielda' (YO) CH&X)OEt 72 CH3(CH&COOEt ni PhCOOEt 62 CH3(CH2)2COOEt 76 84 a) Quenching the reaction at - 10 "C gave the /3. y-unsaturated ketone. 6 Synthesis of Spiro y-Lactones and Spiro S-Lactones from 1,3-Diene-Magnesium Reagents The generation of a quaternary carbon center, and the introduction of functional groups, which are present in the process of lactonization, are some of the difficulties associated with the formation of spirolactones.

2 LiBr-based active copper. 10) (a) 92 42 70 90 94 81 87 92 82 80 45 81 itics have been prepared. The ability of this CuCN-based active copper to tolerate a wide variety of functionalities allows the facile formation of highly functionalized homoallylic alcohols, lJ,y-unsaturated ketones, and amines in exccllcnt ikolated yields. The organocopper rcagents derived from primary allyl chlorides showed a remarkable themostability with littlc decomposition at 0 OC, unlike sccondary allyl organocopper rcagents, which decompose at a significant rate.

3 Scheme 1-9. Synthesis of' spiro-6-lactones. 2 Rieke Mngrlesiirm, Cdcium, Stionriitm, and Rariirin 19 Table 1-8. Reactions of conjugated dienc-magnesium reagents with epoxides followed by carbon dioxide. Entry Diene Epoxide"' Productb) Yieldc) (%) 69 0 To 394 0 63") 5 H YT 72') 0 a) The epoxide was added to the dicne-magnesium complex at -78 "C and the reaction mixture wa.. stirred at -78 "C for 30 min, then gradually warmed to 0 "C followed by the bubbling of COl. b) Elemental analysis, mass spectra, 'H N M R , 13C NMR, and FlTR were all consistent with the indicated formulation.

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