期刊
ORGANIC LETTERS
卷 15, 期 21, 页码 5424-5427出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol402395j
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资金
- Pfizer
- Merck
- EPSRC
- University of York
The asymmetric lithiation trapping of N-Boc heterocycles using s-BuLi/chiral diamines at temperatures up to -20 degrees 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 degrees 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 similar to 90:10 er even at -20 degrees C.
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