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The amount of phosphinc ligands present in the reaction mixture has a pronounced effect upon the yield of the conjugate adduct in these reactions. These results are in agreement with those reported by Noyori, in which a significant enhancement in the yields of the conjugate adducts was observed when using excess PBu3 with the organocopper reagents . Chlorotrimethylsilane is also compatible with the reaction conditions . The low-temperature addition of chlorotrimethylsilane to the organocopper reagents, followed by addition of the enone and subsequent acidic work-up, results in the formation of the 3-alkylated cyclohexanone products in good 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. When MeLi was added to thcse functionalized organocopper species derived from allyl chlorides, an intramolecular opcning of the epoxide produced a bicyclic product, as shown in Scheme 1-14. h , 7 ",I* --1oooc 10 min h ' f I 1 &Cu(CN)Li MeLi -90 OC 15 mh 50 :50 cis & trans mixhue "h 1) -90 to -20 "C 2) H+ AX Me Scheme 1-14 Intrarnolccular epoxide opening to afford a bicyclic product.
4 Organocopper Keagents Utilizing Rieke Copper Table 1-30. Reaction of coppcr anion with organohalidcs and wbsequent cross-coupling reactions with bcnm y 1 chloride. Cu' Complex Entry 1 2 3 4 5 6 7 X 9 10 11 12 Halidc 'C 2 LiNp + : IHF KX - + 35'C Complex CHdCFI2hCI CH3(CH2)7CI CHdCHz)7Cl CH~(CHZ)~R~ CHI(CH~)~CHB~CH~ C6HI ICI CbHllCl PhCl PhBr PhF CH3(CHz)Kl CHdCHd7CI CUI . PPhi CUI PPhi CUI PPh3 CUI. PPh3 CUI . PPh3 CUI PPh3 CUI . PPh3 CUI PPh3 CUI . PPh3 CUI . PPh3 CuCN 2 LiBr CuCN 2 LiBr PhCOCl - -+ -35 C Temp.
Active Metals by Furstner A