The synthesis of optically active P-heterocycles

G. Keglevich, Judit Dvorszki, Viktória Ujj, K. Ludányi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Optically active 1-alkoxy- and 1-amino- 3-phospholene oxides were synthesized by the reaction of the corresponding 1-chloro-3-phospholene oxides with (1 R,2S,5R)-(-)menthol and (S)-(-)-α- phenylethylamine. The 3-methyl-3-phospholene oxides were subjected to dichlorocyclopropanation under liquid-liquid phase transfer catalytic conditions to afford the 3-phosphabicyclo[3.1.0]hexane 3-oxides as a mixture of four diastereomers. Thermolysis of the menthyl-phosphabicyclohexane oxides led to the corresponding 1 2-dihydrophosphinine oxide as a diastereomeric mixture of two double-bond isomers. As a result of additional steps, the dichlorocarbene addition reaction of the 1-menthyl- 3,4-dimethyl-3-phospholene oxide resulted in eventually, the formation of a 4-dichloromethylene-1,4-dihydrophosphinine oxide.

Original languageEnglish
Pages (from-to)271-277
Number of pages7
JournalHeteroatom Chemistry
Volume21
Issue number4
DOIs
Publication statusPublished - 2010

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Oxides
Menthol
Phenethylamines
Lead oxide
Thermolysis
Addition reactions
Liquids
Hexanes
Isomers

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

The synthesis of optically active P-heterocycles. / Keglevich, G.; Dvorszki, Judit; Ujj, Viktória; Ludányi, K.

In: Heteroatom Chemistry, Vol. 21, No. 4, 2010, p. 271-277.

Research output: Contribution to journalArticle

Keglevich, G. ; Dvorszki, Judit ; Ujj, Viktória ; Ludányi, K. / The synthesis of optically active P-heterocycles. In: Heteroatom Chemistry. 2010 ; Vol. 21, No. 4. pp. 271-277.
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