On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

Steven D. Bull, Stephen G. Davies, A. Christopher Garner, Alastair L. Parkes, Paul M. Roberts, Thomas G. R. Sellers, Andrew D. Smith, Juan A. Tamayo, James E. Thomson, Richard J. Vickers

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

High levels of diastereoselectivity are observed for benzylation of the lithium enolates of (S)- N, N'-bis- para-methoxybenzyl-3-iso-propyl-piperazine- 2,5-dione, ( S)- N( 1)- para-methoxybenzyl-N( 4)methyl- 3-iso-propyl-piperazine-2,5-dione and ( S)- N( 1)- methyl- N( 4)- para-methoxybenzyl-3-isopropylpiperazine- 2,5-dione. These data suggest that the high diastereofacial selectivity observed for alkylation of these diketopiperazine templates is mainly a consequence of the relay of stereochemical information from C( 3) to C( 6) via the influence of 1,2-torsional strain introduced by the N-alkyl substituents, rather than through minimisation of steric interactions alone.

Original languageEnglish
Pages (from-to)486-495
Number of pages10
JournalNew Journal of Chemistry
Volume31
Issue number4
DOIs
Publication statusPublished - 2007

Keywords

  • ALPHA-AMINO-ACIDS
  • DIELS-ALDER REACTIONS
  • CHIRAL RELAY
  • ASYMMETRIC-SYNTHESIS
  • ENANTIOSELECTIVE SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • CONJUGATE ADDITION
  • CYCLIC DIPEPTIDES
  • ASSIGNMENT
  • AUXILIARY

Fingerprint

Dive into the research topics of 'On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates'. Together they form a unique fingerprint.

Cite this