Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

Stephen G. Davies, Matthew J. Durbin, Scott J. S. Hartman, Ai Matsuno, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson, Steven M. Toms

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2870-2881
Number of pages12
JournalTetrahedron: Asymmetry
Volume19
Issue number24
DOIs
Publication statusPublished - 12 Dec 2008

Keywords

  • DIASTEREOSELECTIVE CONJUGATE ADDITION
  • HELICAL SECONDARY STRUCTURE
  • HOMOCHIRAL LITHIUM AMIDES
  • BETA-PEPTIDE
  • GRIGNARD-REAGENTS
  • ACIDS
  • 3-ALKYL-CISPENTACIN
  • STEREOCHEMISTRY
  • HEXAPEPTIDE
  • PROTONATION

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