Asymmetric Lithiation Trapping of N-Boc Heterocycles at Temperatures above −78 °C

Giacomo Gelardi, Graeme Barker, Peter O'Brien, David C. Blakemore

Research output: Contribution to journalArticle

Abstract

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.
Original languageEnglish
Pages (from-to)5424-5427
Number of pages4
JournalOrganic Letters
Volume15
Issue number21
Early online date15 Oct 2013
DOIs
Publication statusPublished - 1 Nov 2013

Fingerprint Dive into the research topics of 'Asymmetric Lithiation Trapping of N-Boc Heterocycles at Temperatures above −78 °C'. Together they form a unique fingerprint.

  • Cite this