Asymmetric induction in the reaction of nonsymmetrical phosphinic and phosphinous acid clorides with derivatives of D-glucofuranose

Article abstract of DOI:10.1080/10426509608037959

Reaction of nonsymmetrically substituted chlorophosphines (1-3) with (-)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose (1) or (-)-1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose (5) proceeds with high stereoselectivity to give stereochemically pure phosphinic acid esters (6-8), which are starting compounds for the preparation of chiral organophosphorus compounds. Reaction of benzyl-phenylphosphinous acid chloride with (1) leads to optically pure phosphinous acid ester (9). The stereochemistry of the reaction is studied in dependence on the nature of the base, solvent, temperature and excess of chlorophosphine.

Full text of DOI:10.1080/10426509608037959

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Phosphorus, Sulfur, and Silicon and
the Related Elements
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ASYMMETRIC INDUCTION IN THE
REACTION OF NONSYMMETRICAL
PHOSPHINIC AND PHOSPHINOUS ACID
CLORIDES WITH DERIVATIVES OF D-
GLUCOFURANOSE
Oleg I. Kolodiazhnyi a & Evgen V. Grishkun a
a Institute of Bioorganic Chemistry, National Academy of
Sciences of Ukraine , Murmanskaya Street I, Kiev, 253094,
Ukraine
Published online: 24 Sep 2006.
To cite this article: Oleg I. Kolodiazhnyi & Evgen V. Grishkun (1996) ASYMMETRIC INDUCTION
IN THE REACTION OF NONSYMMETRICAL PHOSPHINIC AND PHOSPHINOUS ACID CLORIDES WITH
DERIVATIVES OF D-GLUCOFURANOSE, Phosphorus, Sulfur, and Silicon and the Related Elements,
115:1, 115-124, DOI: 10.1080/10426509608037959
To link to this article: http://dx.doi.org/10.1080/10426509608037959
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