By A. Furstner
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Additional info for Active Metals [chemistry]
The 1,6conjugate addition of these alkylcopper species with 2-cyclohexenone proceeds readily at -78 "C with the enone being consumed upon warming to -50 "C. In contrast, organocopper species derived using triphenylphosphine gave little or no conjugate addition products. 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 .
PEtl) by a stoichiometric amount of preformed lithium naphthalenide in an ethereal solvcnt under inert, ambient conditions . By using this method the reduction time was substantially shortened. The formation of lithium naphthalenide required 2 h and the subsequent reduction of the coppcr(1) salt complex was usually completcd within 5 min, giving an active coppcr that was much more reactive than previous forms of copper. The resulting copper solutions appeared homogeneous and could be stirred for prolonged periods without sintering.
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. CiS 44 I Rieke Metals: Highly Reactive Mrtul Powders Table 1-29. Reaction of CuCN 2 LiBr-derived copper with 2,3-dichloropropene.