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Extra info for Active Metals
The MeLi is believed to act as a "dummy" non-transfcrable ligand, presumably forming a higher-order cuprate. 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 .
Sium salt of a y-amino acid (5). Acidic hydrolysis followed by warming to 40 "C generated p-( 1-methylethenyl)-/3-methyl-y-phenyl-N-benzyllactam(7)in 67% isolated yield as a 75 : 25 mixture of diastereomers (Table 1-10, entry 2). Importantly, the generation of a highly substituted y-lactam was accomplished in a one-pot process and in good overall chemical yield. This approach was equally applicable to 1,2-bis(methylene)cyclohexane and provided a facile route to a spiro y-lactam, ~-((2-methylene)cyclohexyl)-y-phenyl-Nbenzyllactam in 36% isolated yield (Table 1-10, entry 5).
Entry El E2 PhCHO H+ 88 A PhCHO Yield (YO) Product P h 69 12 U P h XPh PhCHO 71 PhCHO 83 PhCHO 63 x: U PhCHlCOCH? 7 8 /VC' P h 22 NCH2Ph I1 PhCH This highly reactive copper derived from CuCN . 2 LiCl reacts directly with 2,3-dichloropropene to yield a new bis-organocopper species which contains both a nucleophilic allylic and a vinylic moiety . This novel bis-organocopper reagent undergoes a selective onepot addition to two different electrophiles in good to excellent yields. The more reactive allyl carbon-copper bond adds to the first electrophile, followed by the incorporation of the second electrophile into the vinyl carbon-copper bond.