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Extra info for Active Metals
This is a significant finding in that this is a regiospecific 5-exo-trig cyclization which can occur in the prcsence of functional groups, with the possibility of further functionalization with various electrophiles. This methodology can be extended to w-alkenyl-sec-alkylzinc reagents as well as the tcrtiary organozinc iodide reagents . 3 Rieke Zinc 31 Rieke Lint can be quite useful in the generation of heteroarylzinc halide reagents. Pyridinylzinc halides can be formed from bromo- or iodopyridines and Rieke zinc at room temperature 1631.
Primary and secondary allyl chlorides containing diverse functionalities are tolerated by the CuCN-based copper. -unsaturated ketone, epoxide, nitrile, alkyl acetate, ester, alkyl chloride, and carbamate functionalTable 1-27. Cross-coupling of benzoyl chloride with organocopper reagents dcrived from CuCN . 2 LiRrbased active copper. r Reagents Iltilizing Hiekc, Copper 43 Table 1-28. Conjugatc additions with organocoppcr reagents derived from CuCN . 2 LiBr-based active copper. 10) (a) 92 42 70 90 94 81 87 92 82 80 45 81 itics have been prepared.
Much work has been done to elucidate novel synthetic routes for these types of molecules . In particular, d-substituted d-lactones have recently attracted considerable attention, mainly because molecules of this class include many natural products that exhibit significant biological activity . Scheme 1-9 illustrates a route for the synthesis of spiro d-lactones from the magnesium complex of 1,2-bis(methylene)cyclohexane 1 . Initially, treatment of the 1,2bis(methy1ene)cyclohexane-magnesium reagent 2 with an excess of ethylene oxide at -78 "C resulted in the formation of the 1,2-adduct 3 by the incorporation of one equivalent of epoxide with the diene complex.