By A. Furstner
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Extra resources for Active Metals [chemistry]
22 I Rieke Metals: Higlily Reactive Metal Powders tams. The protccting groups can then be easily removed under a variety of conditions 1481. This efficient radical cyclization route to cis-fused pyrrolidones and piperidones is interesting because of the widespread occurrence of related systems in natural products . We have recently developed a direct method for the one-pot synthesis of y-lactams and secondary amines utilizing conjugated dicne-magnesium complexes [ S O ] . 3-dimethyl2-butene- 1,4-diyl)magnesiurn intermediate (2).
CiS 44 I Rieke Metals: Highly Reactive Mrtul Powders Table 1-29. Reaction of CuCN 2 LiBr-derived copper with 2,3-dichloropropene. 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 U PhCHlCOCH? /VC' P h x: 22 7 8 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.
For example, treatment of 6-bromo- 1,2-epoxyhexane with thienyl-based copper resulted in intramolecular cyclization; subsequent trapping of the intermediate with benzoyl chloride gave a 64 : 36 mixture of cyclohexyl benzoate and cyclopentylmethyl benzoate in 52% isolated yield as shown in Scheme 1-13. 52% (64:36) awi Scheme 1-13. Intramolecular cyclizations via epoxide cleavage. 5 Copper Cyanide-Based Active Copper Initial attempts to make active copper from CuCN . nLiX complexes (X = Br, C1) met with only limited success.