Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates

Julien Lefranc, Alberto Minassi, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

5 Citations (Scopus)

Abstract

N-Alkenyl ureas and N-alkenyl carbamates, like other N-acyl enamines, are typically nucleophilic at their β-carbon. However, by incorporating an α-aryl substituent, we show that they will also undergo attack at the β-carbon by organolithium nucleophiles, leading to the products of carbolithiation. The carbolithiation of E and Z N-alkenyl ureas is diastereospecific, and N-tert-butoxy-carbonyl N-alkenyl carbamates give carbolithiation products that may be deprotected in situ to provide a new connective route to hindered amines.

Original languageEnglish
Pages (from-to)628-632
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
Publication statusPublished - 28 Mar 2013

Keywords

  • Carbamate
  • Carbolithiation
  • Carbometallation
  • Organolithium
  • Stereospecificity
  • Styrene
  • Urea

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