Synthesis of diastereomeric bis(oxazoline) ligands derived from (S,S)-1,1′-bis(4-isopropyloxazolin-2-yl)ferrocene

Ross A. Arthurs, Christopher J. Richards

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)
8 Downloads (Pure)

Abstract

Starting from (S,S)-1,1′-bis(4-isopropyloxazolin-2-yl)ferrocene, all possible 2-trimethylsilyl- and 2,2′-di(trimethylsilyl)-substituted diastereoisomers, potential bisoxazoline ligands for use in asymmetric catalysis, were synthesised by selective lithiation followed by addition of trimethylsilyl chloride. Access to the (S,S,R p,R p)-diastereoisomer was achieved following diastereoselective introduction of two deuterium-blocking groups and utilisation of the high k H/k D value for lithiation, methodology that was also applied to the synthesis of a related 2,2′-di(diphenylmethanol)bisoxazoline ligand.
Original languageEnglish
Pages (from-to)585-588
Number of pages4
JournalSynlett
Volume29
Issue number5
Early online date15 Jan 2018
DOIs
Publication statusPublished - 1 Mar 2018

Cite this