Functionalized phospholanes and phosphorinanes from 1,4- and 1,5-diketones

Abstract

Phosphorylation reactions of 1,4‐diketones, 1,5‐diketones, and methylene‐1,5‐diketones with bidentate phosphorus nucleophiles (phosphines and phosphonous acid derivatives) represent convenient methods of synthesis of saturated functionalized phospholanes and phosphorinanes. © 1997 John Wiley & Sons, Inc. Heteroatom Chem 8: 217–223, 1997.

A Novel Method for the Separation of Bis(α-hydroxyalkyl)phosphinic Acid Diastereoisomers via Formation of Novel Cyclic Phosphinic Acids

“…In the past decade, α-functionalized phosphinic acid derivatives have attracted a great deal of attention due to their usefulness both in medicinal and in material chemistry. − Among α-functionalized phosphinic acids, α-hydroxyphosphinic acids are an important class of compounds that exhibit a variety of interesting and useful properties. − Some α-hydroxyphosphinic acids are useful intermediates for α-hydroxyphosphinyl peptides, showing good inhibitory activity against renin . Symmetric or pseudo-symmetric bis(α-hydroxyalkyl)phosphinic acid derivatives have also drawn attention in the designs of HIV protease inhibitors. , Moreover, α-hydroxyphosphinic acid derivatives are useful intermediates in the synthesis of other phosphorus compounds of material interest that are used as organophosphorus polymers possessing flame-resistant, corrosion-resistant, ion-exchange properties and as extractants for the recovery or separation of some metal ions. − As a part of our effort to explore the utility of microwave-assisted reactions for the synthesis of organophosphorus compounds, we recently described a new method for the synthesis and separation of bis(α-hydroxyalkyl)phosphinic acids from the reactions of hypophosphorous acid with aldehydes using microwave irradiation. , Herein, we report on new aspects of the microwave-assisted reaction of hypophosphorus acid with aldehydes, which are applicable for the separation of bis(α-hydroxyalkyl)phosphinic acid diastereoisomers via formation of novel cyclic phosphinic acids under microwave irradiation.…”

“…1-8 Among R-functionalized phosphinic acids, R-hydroxyphosphinic acids are an important class of compounds that exhibit a variety of interesting and useful properties. [9][10][11][12][13][14][15][16] Some R-hydroxyphosphinic acids are useful intermediates for R-hydroxyphosphinyl peptides, showing good inhibitory activity against renin. 17 Symmetric or pseudo-symmetric bis(R-hydroxyalkyl)phosphinic acid derivatives have also drawn attention in the designs of HIV protease inhibitors.…”