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The Synthesis of Novel Oxazolinylphosphinic Esters and Amides and Application to the Cyanosilylation of Aldehydes

[ Vol. 12 , Issue. 5 ]


Mei Luo   Pages 660 - 672 ( 13 )


A new class of modular functionalized oxazolines are synthesized using a simple, novel one-pot method under inert moisture-free conditions. Then the oxazolines can be further elaborated to phosphine-containing oxazolines. The first step is to synthesize intermediates via the reaction of 2 - hydroxybenzonitrile or 2- aminobenzonitrile with chiral amino alcohols, subsequent reactions with phosphine chlorides, providing products in moderate yields. Product structures are fully characterized by NMR, IR, MS and X-Ray analyses. These compounds are found to be highly active catalysts for the cyanosilylation of prochiral benzaldehyde (20-96% yield).


Functionalized oxazolines, chiral organometallic complexes, 2-hydroxybenzonitrile, 2- aminobenzonitrile, chiral amino alcohols, phosphine chlorides.


Hefei University of Technology, Department of Chemical Engineering, Hefei, 230009, China.

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