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Asymmetric lithiation trapping of N -boc heterocycles at temperatures above -78°C

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Publication details

JournalOrganic Letters
DateE-pub ahead of print - 15 Oct 2013
DatePublished (current) - 1 Nov 2013
Issue number21
Number of pages4
Pages (from-to)5424-5427
Early online date15/10/13
Original languageEnglish


The asymmetric lithiation trapping of N-Boc heterocycles using s-BuLi/chiral diamines at temperatures up to -20°C is reported. Depending on the N-Boc heterocycle, lithiation is accomplished using s-BuLi and (-)-sparteine or the (+)-sparteine surrogate in the temperature range -50 to -20°C for short reaction times (2-20 min). Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered functionalized N-Boc heterocycles in 47-95% yield and 77:23-93:7 er. With N-Boc pyrrolidine, trapped products can be generated in ∼90:10 er even at -20°C.

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