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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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

Author(s): Mei Luo

Volume 12, Issue 5, 2015

Page: [660 - 672] Pages: 13

DOI: 10.2174/157017941205150821153905

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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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