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

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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

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Keywords

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

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