- Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF.
Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF.
Organic letters (2010-08-20)
Graeme Barker, Peter O'Brien, Kevin R Campos
PMID20718476
ABSTRACT
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.
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