Abstract
The synthesis of a new series of arylhydroxymethylphosphinic acid derivatives is described.
The protected compounds were prepared by a palladium(0) catalysed arylation of ethyl
benzyloxymethylphosphinate with aryl halides. Subsequent hydrogenolysis of the benzyl
protecting group followed by acidic hydrolysis of the ester function readily afforded
the target compounds. Selective removal of the ester group was achieved by basic hydrolysis
whereas acidic hydrolysis directly gave the totally deprotected compounds.
Key words
phosphorus - phosphinates - palladium - arylations - protecting groups
References
<A NAME="RP04203SS-1">1 </A>
Fields SC.
Tetrahedron
1999,
55:
12237
<A NAME="RP04203SS-2">2 </A>
Kafarski P.
Lejczak B. Phosphorous Sulfur Silicon
1991,
63:
193
<A NAME="RP04203SS-3">3 </A>
Kukhar VP.
Hudson HR. In Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity
John Wiley & Sons Ltd;
Chichester, UK:
2000.
<A NAME="RP04203SS-4">4 </A>
Cristau H.-J.
Coulombeau A.
Genevois-Borella A.
Sanchez F.
Pirat J.-L.
J. Organomet. Chem.
2002,
643-645:
381
<A NAME="RP04203SS-5">5 </A>
Schuman M.
Lopez X.
Karplus M.
Gouverneur V.
Tetrahedron
2001,
57:
10299
<A NAME="RP04203SS-6">6 </A>
Lei H.
Stoakes MS.
Schwabacher AW.
Synthesis
1992,
1255
<A NAME="RP04203SS-7">7 </A>
Johansson T.
Stowinski J.
Chem. Commun.
2001,
2564
<A NAME="RP04203SS-8">8 </A>
Lei H.
Stoakes MS.
Herath KPB.
Lee J.
Schwabacher AW.
J. Org. Chem.
1994,
59:
4206
<A NAME="RP04203SS-9">9 </A>
Petrakis KS.
Nagabhushan TL.
J. Am. Chem. Soc.
1987,
109:
2831
<A NAME="RP04203SS-10">10 </A>
Ma D.
Tian H.
J. Chem. Soc, Perkin Trans. 1
1997,
3493
<A NAME="RP04203SS-11">11 </A>
Ma D.
Zhu W.
J. Org. Chem.
2001,
66:
348
<A NAME="RP04203SS-12">12 </A>
Cristau H.-J.
Brahic C.
Pirat J.-L.
Tetrahedron
2001,
57:
9149
<A NAME="RP04203SS-13">13 </A>
Sietsema WK.
Ebetino FH.
Exp. Opin. Invest. Drugs
1994,
3:
1255
<A NAME="RP04203SS-14">14 </A>
Xu Y.
Li Z.
Xia J.
Guo H.
Huang Y.
Synthesis
1983,
377
<A NAME="RP04203SS-15">15 </A>
Xu J.
Zhang J.
Synthesis
1984,
778
<A NAME="RP04203SS-16">16 </A>
Xu Y.
Zhang J.
J. Chem. Soc., Chem. Commun.
1986,
1606
<A NAME="RP04203SS-17">17 </A>
Zhang J.
Xu Y.
Huang G.
Guo H.
Tetrahedron Lett.
1988,
1955
<A NAME="RP04203SS-18">18 </A>
Montchamp J.-L.
Dumond YR.
J. Am. Chem. Soc.
2001,
123:
510
<A NAME="RP04203SS-19">19 </A>
Bennett SNL.
Hall RG.
J. Chem. Soc., Perkin Trans. 1
1995,
1145
<A NAME="RP04203SS-20">20 </A>
Lei H.
Stoakes MS.
Herath KPB.
Lee J.
Schwabacher AW.
J. Org. Chem.
1994,
4206
<A NAME="RP04203SS-21">21 </A>
Luke GP.
Shakespeare WC.
Synth. Commun.
2002,
2951
<A NAME="RP04203SS-22">22 </A>
Baylis EK.
Tetrahedron Lett.
1995,
36:
9389
<A NAME="RP04203SS-23">23 </A>
Cristau H.-J.
Virieux D.
Tetrahedron Lett.
1999,
40:
703
<A NAME="RP04203SS-24">24 </A>
Boyd EA.
Regan AC.
James K.
Tetrahedron Lett.
1992,
33:
813
<A NAME="RP04203SS-25">25 </A>
Boyd EA.
Regan AC.
James K.
Tetrahedron Lett.
1994,
35:
4223
<A NAME="RP04203SS-26">26 </A>
Chen S.
Cowards JK.
J. Org. Chem.
1998,
63:
502
<A NAME="RP04203SS-27">27 </A>
Dumond R.
Backer LR.
Montchamp JL.
Org. Lett.
2000,
2:
3341
<A NAME="RP04203SS-28">28 </A>
Hartung WH.
Simonoff R.
Rorer WR.
Org. React.
Vol. VII:
Wiley;
London:
1953.
p.263-326
<A NAME="RP04203SS-29">29 </A>
Heathcock CH.
Ratcliffe R.
J. Am. Chem. Soc.
1971,
93:
1746
<A NAME="RP04203SS-30">30 </A>
Kudzin ZH.
Stec WJ.
Synthesis
1978,
469
<A NAME="RP04203SS-31">31 </A>
Yuan C.
Chen D.
Synthesis
1992,
531
<A NAME="RP04203SS-32">32 </A>
Boduszek B.
Tetrahedron
1996,
52:
12483
<A NAME="RP04203SS-33">33 </A>
Bartlett PA.
Hanson JE.
Giannousis PP.
J. Org. Chem.
1990,
55:
6228
