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Ili:ing Rieke Copper 41 Table 1-26. Reactions of thienyl-based organocopper reagents with 1,2-epoxybutane. Entry Halide Product Yield (%) 71 60 68 64 78 62 . Both cyclic and acyclic enones worked well with this formulation of active copper. However, more sterically hindered enones, such as isophorone, carvone, and 2,4,4-~imethyl-Zcyclohexen- 1-one, were not amenable for these 1,4-conjugatc additions. The thienyl-based organocopper reagents were also found to be nucleophilic enough to undergo intermolecular epoxide-opening reactions with 1,2-epoxybutane to form single regioisomers in good isolated yields, as shown in Table 1-26.
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.
Unfortunately, arylzinc compounds did not yield the S N ~product ' when reacted with 1,4-dichloro-2-butyne. However, when reacted with 1,4-ditosyloxy-2butyne, aryl and alkyl organozincs gave excellent yields of the Ss2' products. Table 1- 16 shows examples of this type of transformation. The use of Rieke zinc allows a wide varety of functional groups to be included . This same catalyst can be used to make 2-halo-olefins incorporating a high degree of functionality by reacting with 2,3-dibromopropene 1591.