An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines: Preparation of trans-DHQs

Jens Mortansson Jelstrup Nolsøe, David Riegert, Paul Müller, David Ackland Tanner

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

As an approach to the enantioselective synthesis of trans-decahydroquinolines (DHQs), desymmetrization of meso-aziridine (5) with various carbon nucleophiles under catalytic conditions was investigated. By applying TMSCN in the presence of YbCl3 and chiral nonracemic ligands, nitrile 13 was obtained with an ee up to 40%. Nitrile 13 was a key intermediate in a novel route to trans-DHQs.
Original languageEnglish
JournalCollection of Czechoslovak Chemical Communications
Volume76
Issue number7
Pages (from-to)815-828
ISSN0010-0765
DOIs
Publication statusPublished - 2011

Bibliographical note

Dedicated to Professor Pavel Kočovský on the occasion of his 60th birthday.

Keywords

  • Synthetic methods
  • Alkaloids
  • Desymmetrization
  • Metathesis
  • trans-DHQs
  • Yb-catalysis
  • meso-Aziridines

Cite this