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

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

Research output: Contribution to journalArticle

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.
Original languageEnglish
Pages (from-to)4176-4179
Number of pages4
JournalOrganic Letters
Volume12
Issue number18
Early online date18 Aug 2010
DOIs
Publication statusPublished - 17 Sep 2010

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Piperazines
Imidazolidines
Pyrrolidines
Diamines

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Barker, Graeme ; O'Brien, Peter ; Campos, Kevin R. / Diamine-Free Lithiation−Trapping of N-Boc Heterocycles using s-BuLi in THF. In: Organic Letters. 2010 ; Vol. 12, No. 18. pp. 4176-4179.
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Diamine-Free Lithiation−Trapping of N-Boc Heterocycles using s-BuLi in THF. / Barker, Graeme; O'Brien, Peter; Campos, Kevin R.

In: Organic Letters, Vol. 12, No. 18, 17.09.2010, p. 4176-4179.

Research output: Contribution to journalArticle

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