Designed ligands as probes for the catalytic binding mode in Mo-catalyzed asymmetric allylic alkylation

Barry M. Trost, Kalindi Dogra, Iwao Hachiya, Takashi Emura, David L. Hughes, Shane Krska, Robert A. Reamer, Michael Palucki, Nobuyoshi Yasuda, Paul J. Reider

Research output: Contribution to journalArticle

89 Scopus citations

Abstract

Unusual coordination in the asymmetric allylic alkylation catalyzed by molybdenum (see scheme) was revealed by a study on several ligands, for example, 1. Unexpectedly, only the nitrogen atom of one picolinamide group coordinates to Mo, while the other amide group rigidifies the system. Based on the effectiveness of the bisdeprotonated ligand, the observed reaction can be rationalized and new ligands can be designed for asymmetric induction in allylic alkylations.

Original languageEnglish (US)
Pages (from-to)1929-1932
Number of pages4
JournalAngewandte Chemie - International Edition
Volume41
Issue number11
DOIs
StatePublished - Jun 3 2002

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Allylic compounds
  • Asymmetric catalysis
  • Ligand design
  • Molybdenum
  • Regioselectivity

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