A chiral ligand mediated aza-conjugate addition strategy for the enantioselective synthesis of β-amino esters that contain hydrogenolytically sensitive functionality

Robert M. Archer, Marc Hutchby, Caroline L. Winn, John S. Fossey, Steven D. Bull

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Aza-conjugate addition of the lithium anion of N-trimethylsilyl-p-methoxybenzylamine to tert-butyl enoate acceptors, in the presence of a stoichiometric amount of enantiopure 1,2-dimethoxy-1,2-diphenylethane and excess trimethylsilyl chloride, affords tert-butyl-N-p-methoxybenzyl-β-amino esters with excellent levels of enantiocontrol. These N-p-methoxybenzyl-β-amino-esters may be deprotected under oxidative conditions via treatment with ceric ammonium nitrate, followed by acid hydrolysis of the resultant imine intermediates, to afford enantiopure β-amino-esters containing hydrogenolytically sensitive functionality.

Original languageEnglish
Article number27040
Pages (from-to)8838-8847
Number of pages10
JournalTetrahedron
Volume71
Issue number46
Early online date14 Aug 2015
DOIs
Publication statusPublished - 18 Nov 2015

Fingerprint

Esters
Ligands
Imines
Lithium
Anions
Hydrolysis
Acids
4-methoxybenzylamine
1,2-dihydrostilbene
trimethylsilyl chloride
ceric ammonium nitrate

Keywords

  • Aza-conjugate addition
  • Enantioselective synthesis
  • External chiral ligand
  • Oxidative deprotection
  • β-Amino esters

Cite this

A chiral ligand mediated aza-conjugate addition strategy for the enantioselective synthesis of β-amino esters that contain hydrogenolytically sensitive functionality. / Archer, Robert M.; Hutchby, Marc; Winn, Caroline L.; Fossey, John S.; Bull, Steven D.

In: Tetrahedron, Vol. 71, No. 46, 27040, 18.11.2015, p. 8838-8847.

Research output: Contribution to journalArticle

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AU - Bull, Steven D.

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