Resolution of 1-n-propoxy-3-methyl-3-phospholene 1-oxide by diastereomeric complex formation using TADDOL derivatives and calcium salts of O,O′-dibenzoyl-(2R,3R)- or O,O′-di-p-toluoyl-(2R,3R)-tartaric acid

Péter Bagi, M. Kállay, Dóra Hessz, M. Kubinyi, Tamás Holczbauer, M. Czugler, E. Fogassy, G. Keglevich

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12 Citations (Scopus)

Abstract

1-n-Propoxy-3-methyl-3-phospholene 1-oxide was prepared in optically active form by extending resolution methods applying (-)-(4R,5R)-4,5- bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ('TADDOL') and (-)-(2R,3R)-α,α,α′,α′-tetraphenyl-1, 4-dioxaspiro[4.5]decan-2,3-dimethanol ('spiro-TADDOL'), as well as the acidic and neutral Ca2+ salts of (-)-O,O′-dibenzoyl- and (-)-O,O′-di-p-toluoyl-(2R,3R)-tartaric acid. In one case, the diastereomeric complex could be identified by single crystal X-ray analysis. The absolute P-configuration of the enantiomers of the phospholene oxide was also determined by CD spectroscopy.

Original languageEnglish
Pages (from-to)318-326
Number of pages9
JournalTetrahedron Asymmetry
Volume25
Issue number4
DOIs
Publication statusPublished - Feb 28 2014

Fingerprint

Oxides
calcium
Calcium
Salts
salts
Derivatives
acids
oxides
Acids
Enantiomers
enantiomers
X ray analysis
Single crystals
Spectroscopy
single crystals
configurations
spectroscopy
x rays
tartaric acid

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

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title = "Resolution of 1-n-propoxy-3-methyl-3-phospholene 1-oxide by diastereomeric complex formation using TADDOL derivatives and calcium salts of O,O′-dibenzoyl-(2R,3R)- or O,O′-di-p-toluoyl-(2R,3R)-tartaric acid",
abstract = "1-n-Propoxy-3-methyl-3-phospholene 1-oxide was prepared in optically active form by extending resolution methods applying (-)-(4R,5R)-4,5- bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ('TADDOL') and (-)-(2R,3R)-α,α,α′,α′-tetraphenyl-1, 4-dioxaspiro[4.5]decan-2,3-dimethanol ('spiro-TADDOL'), as well as the acidic and neutral Ca2+ salts of (-)-O,O′-dibenzoyl- and (-)-O,O′-di-p-toluoyl-(2R,3R)-tartaric acid. In one case, the diastereomeric complex could be identified by single crystal X-ray analysis. The absolute P-configuration of the enantiomers of the phospholene oxide was also determined by CD spectroscopy.",
author = "P{\'e}ter Bagi and M. K{\'a}llay and D{\'o}ra Hessz and M. Kubinyi and Tam{\'a}s Holczbauer and M. Czugler and E. Fogassy and G. Keglevich",
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TY - JOUR

T1 - Resolution of 1-n-propoxy-3-methyl-3-phospholene 1-oxide by diastereomeric complex formation using TADDOL derivatives and calcium salts of O,O′-dibenzoyl-(2R,3R)- or O,O′-di-p-toluoyl-(2R,3R)-tartaric acid

AU - Bagi, Péter

AU - Kállay, M.

AU - Hessz, Dóra

AU - Kubinyi, M.

AU - Holczbauer, Tamás

AU - Czugler, M.

AU - Fogassy, E.

AU - Keglevich, G.

PY - 2014/2/28

Y1 - 2014/2/28

N2 - 1-n-Propoxy-3-methyl-3-phospholene 1-oxide was prepared in optically active form by extending resolution methods applying (-)-(4R,5R)-4,5- bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ('TADDOL') and (-)-(2R,3R)-α,α,α′,α′-tetraphenyl-1, 4-dioxaspiro[4.5]decan-2,3-dimethanol ('spiro-TADDOL'), as well as the acidic and neutral Ca2+ salts of (-)-O,O′-dibenzoyl- and (-)-O,O′-di-p-toluoyl-(2R,3R)-tartaric acid. In one case, the diastereomeric complex could be identified by single crystal X-ray analysis. The absolute P-configuration of the enantiomers of the phospholene oxide was also determined by CD spectroscopy.

AB - 1-n-Propoxy-3-methyl-3-phospholene 1-oxide was prepared in optically active form by extending resolution methods applying (-)-(4R,5R)-4,5- bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ('TADDOL') and (-)-(2R,3R)-α,α,α′,α′-tetraphenyl-1, 4-dioxaspiro[4.5]decan-2,3-dimethanol ('spiro-TADDOL'), as well as the acidic and neutral Ca2+ salts of (-)-O,O′-dibenzoyl- and (-)-O,O′-di-p-toluoyl-(2R,3R)-tartaric acid. In one case, the diastereomeric complex could be identified by single crystal X-ray analysis. The absolute P-configuration of the enantiomers of the phospholene oxide was also determined by CD spectroscopy.

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