Stereoselective synthesis and molecular modeling of chiral cyclopentanes

Raid J. Abdel-Jalil, Thomas Steinbrecher, Thuraya Al-Harthy, Ahmed Mahal, Osama K. Abou-Zied, Wolfgang Voelter

Research output: Contribution to journalArticle

Abstract

Abstract The reaction of 3-methyseleno-2-methylselenomethyl-propene with benzyl 2,3-anhydro-4-O-triflyl-β-L-ribopyranoside provides a major convenient enantiomeric product of 1-methylene-(benzyl3,4-dideoxy-α-D-arabinopyranoso)-[3,4-c]-cyclopentane, with benzyl-2,3-anhydro-4-deoxy-4-C-(2-methyl- propen-3-yl)-α-D-lyxopyranoside as a minor product. While the reaction of 3-methyseleno-2-[methylselenomethyl]-propene with benzyl 2,3-anhydro-4-O-triflyl-α-D-ribopyranoside produces a good yield of benzyl-2,3-anhydro-4-deoxy-4-C-(2-methylpropen-3-yl)-α-D-lyxo-pyranoside. Molecular modeling and molecular dynamics simulations indicate that the intermediate in the reaction of the β-L sugar frequently occupies an optimal conformation that leads to the formation of cyclopentane, while the intermediate in the reaction of the α-D sugar has a very small probability. The results point to the dominant role of the β-L sugar intermediate in controlling the cyclopentane formation.

Original languageEnglish
Article number7038
Pages (from-to)12-16
Number of pages5
JournalCarbohydrate Research
Volume415
DOIs
Publication statusPublished - Aug 11 2015

Keywords

  • Asymmetric synthesis
  • Cyclopentane
  • Molecular dynamics
  • Molecular modeling

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective synthesis and molecular modeling of chiral cyclopentanes'. Together they form a unique fingerprint.

  • Cite this