By the same authors

From the same journal

From the same journal

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

Research output: Contribution to journalArticlepeer-review

Published copy (DOI)

Author(s)

Department/unit(s)

Publication details

JournalOrganic Letters
DateE-pub ahead of print - 15 Oct 2013
DatePublished (current) - 1 Nov 2013
Issue number21
Volume15
Number of pages4
Pages (from-to)5424-5427
Early online date15/10/13
Original languageEnglish

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.

Discover related content

Find related publications, people, projects, datasets and more using interactive charts.

View graph of relations