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Palladium/BINAP(S)-catalyzed asymmetric allylic amination.

J W Faller1, Jeremy C Wilt

  • 1Department of Chemistry, Yale University, New Haven, CT 06520, USA. jack.faller@yale.edu

Organic Letters
|February 12, 2005
PubMed
Summary

This study explores palladium-catalyzed enantioselective allylic amination using BINAP(S) ligands. High enantioselectivity (ee) and regioselectivity for branched isomers were achieved with various substrates.

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Area of Science:

  • Organometallic Chemistry
  • Asymmetric Catalysis
  • Synthetic Organic Chemistry

Background:

  • Palladium catalysis is crucial for C-N bond formation.
  • Enantioselective synthesis requires chiral ligands to control stereochemistry.
  • Allylic amination offers a route to valuable amine-containing molecules.

Purpose of the Study:

  • To investigate the enantioselective allylic amination of acyclic allylic carbonates.
  • To evaluate the efficiency of palladium/(S)-BINAP(S) catalyst systems.
  • To explore the impact of modified BINAP(S) ligands on selectivity.

Main Methods:

  • Enantioselective allylic amination reactions using palladium catalysts.
  • Screening of various acyclic allylic carbonate substrates.
  • Utilizing chiral BINAP(S) ligands, including (S)-TolBINAP(S) and (S)-3,5-xylyl-BINAP(S).
  • X-ray crystallography to determine ligand binding mode.

Main Results:

  • High enantioselectivity (ee) was achieved for amination of several substrates.
  • Crotyl carbonates exhibited high regioselectivity for the branched isomer.
  • Modified BINAP(S) ligands, (S)-TolBINAP(S) and (S)-3,5-xylyl-BINAP(S), enhanced enantioselectivity.
  • X-ray crystallography confirmed a P,S binding mode for the BINAP(S) ligand.

Conclusions:

  • The palladium/(S)-BINAP(S) system is effective for enantioselective allylic amination.
  • Ligand modification can significantly improve catalytic performance.
  • Understanding the ligand binding mode aids in catalyst design.

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