4.4 Article

Novel One-Pot Access to Diastereoisomeric Tertiary Phospholanes Oxides by Using Enantiomerically Pure Phospholane Oxides Under Catalyst-Free Conditions

Journal

CHEMISTRYSELECT
Volume 5, Issue 1, Pages 379-383

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201903760

Keywords

Cyclic enantiopure; H-diphenyl phosphine oxide; Kabachnik-Fields reaction; Multicomponent reactions; Secondary phosphine oxides; Tertiary phosphine oxides

Funding

  1. Algerian Ministry of Higher Education and Scientific Research (MESRS, FNR 2000)

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For the first time, enantiopure 1-r-oxo-2-c,5-t-diphenylphospholane was introduced as nucleophile in the multicomponent condensation reaction. Diastereoisomers of 2,5-diphenyl-1-oxo-1-[alkylphenyl-1-(phenylamino) methyl] phospholane derivatives were synthesized by one-pot process from aromatic aldehydes, anilines and enantiopure1-r-oxo-2-c,5-t-diphenylphospholane under green and eco-compatible conditions. The reaction proceeds under catalyst-free conditions at room temperature within very short time (3 min) in excellent yields (up to 95%). An X-ray crystal structure has been obtained for 2,5-diphenyl-1-oxo-1-[phenyl (phenylamino) methyl] phospholane.

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