Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF
- PMID: 20718476
- DOI: 10.1021/ol1017799
Diamine-free lithiation-trapping of N-Boc heterocycles using s-BuLi in THF
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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