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Diamine-Free Lithiation−Trapping of N -Boc Heterocycles using s -BuLi in THF

2010; American Chemical Society; Volume: 12; Issue: 18 Linguagem: Inglês

10.1021/ol1017799

1523-7060

Graeme Barker, Peter O’Brien, Kevin R. Campos,

Synthesis and characterization of novel inorganic/organometallic compounds

A diamine-free protocol for the s-BuLi-mediated lithiation−trapping of N-Boc heterocycles has been developed. In the optimized procedure, lithiation is accomplished using s-BuLi in THF at −30 °C for only 5 or 10 min. Subsequent electrophilic trapping or transmetalation−Negishi coupling delivered a range of functionalized pyrrolidines, imidazolidines, and piperazines in 43−83% yield.