Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism

Josep Comelles, Alex Pericas, Marcial Moreno-Mañas, Adelina Vallribera, Galí Drudis-Solé, Agusti Lledos, Teodor Parella, Anna Roglans, Santiago García-Granda, Laura Roces-Fernández

Research output: Contribution to journalArticleResearchpeer-review

84 Citations (Scopus)

Abstract

High enantioselection is obtained in Michael additions of cyclic β-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and β-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations. © 2007 American Chemical Society.
Original languageEnglish
Pages (from-to)2077-2087
JournalJournal of Organic Chemistry
Volume72
Issue number6
DOIs
Publication statusPublished - 16 Mar 2007

Fingerprint Dive into the research topics of 'Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism'. Together they form a unique fingerprint.

Cite this