Resolution of 3-methyl-3-phospholene 1-oxides by molecular complex formation with TADDOL derivatives

Tibor Novák, J. Schindler, Viktória Ujj, M. Czugler, E. Fogassy, G. Keglevich

Research output: Contribution to journalArticle

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Abstract

The antipodes of 1-phenyl-3-methyl-3-phospholene 1-oxide 1a were separated in good yield and in high enantiomeric excess (∼99% ee) by resolution via formation of diastereomeric complexes with (4R,5R)-(-)- and (4S,5S)-(+)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane 2 (TADDOL) or (-)-(2R,3R)-α,α,α′,α′-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol 3. The method was also suitable for the resolution of the 1-ethoxy-3-phospholene derivative 1b, suggesting that our novel procedure may be of general value, both for the resolution of chiral phosphine oxides and phosphinates.

Original languageEnglish
Pages (from-to)2599-2602
Number of pages4
JournalTetrahedron Asymmetry
Volume17
Issue number18
DOIs
Publication statusPublished - Oct 16 2006

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phosphine
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ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Resolution of 3-methyl-3-phospholene 1-oxides by molecular complex formation with TADDOL derivatives. / Novák, Tibor; Schindler, J.; Ujj, Viktória; Czugler, M.; Fogassy, E.; Keglevich, G.

In: Tetrahedron Asymmetry, Vol. 17, No. 18, 16.10.2006, p. 2599-2602.

Research output: Contribution to journalArticle

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