Preparation of enantiopure 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes

Péter Bagi, Kinga Juhász, M. Kállay, Dóra Hessz, M. Kubinyi, E. Fogassy, G. Keglevich

Research output: Contribution to journalArticle

Abstract

The resolution of 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes using TADDOL derivatives or the Ca2+-salts of tartaric acid derivatives was studied. Both enantiomers of the 1-isopentyl-3-phospholene oxide were prepared in an enantiopure form with (R,R)-spiro-TADDOL, or with the acidic Ca2+-salt of O,O′-dibenzoyl-(R,R)-tartaric acid. The absolute configuration of the 1-isopentyl-3-phospholene oxide enantiomer with negative optical rotation was also substantiated by a study involving CD spectroscopy and theoretical calculations.

Original languageEnglish
Article numbere21411
JournalHeteroatom Chemistry
Volume29
Issue number1
DOIs
Publication statusPublished - Jan 1 2018

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Oxides
Enantiomers
Salts
Optical rotation
Derivatives
Spectroscopy
tartaric acid

Keywords

  • 3-Phospholene oxide
  • CD-spectroscopy
  • diastereomeric associate
  • optical resolution
  • P-stereogenic center

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Preparation of enantiopure 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes. / Bagi, Péter; Juhász, Kinga; Kállay, M.; Hessz, Dóra; Kubinyi, M.; Fogassy, E.; Keglevich, G.

In: Heteroatom Chemistry, Vol. 29, No. 1, e21411, 01.01.2018.

Research output: Contribution to journalArticle

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