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

Author(s): Mei Luo.

Journal Name: Current Organic Synthesis

Volume 12 , Issue 5 , 2015

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Abstract:

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).

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

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Article Details

VOLUME: 12
ISSUE: 5
Year: 2015
Page: [660 - 672]
Pages: 13
DOI: 10.2174/157017941205150821153905

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