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Polystyrene-Supported Enantiopure 1,2-Diamines: Development of a Most Practical Catalyst for the Asymmetric Transfer Hydrogenation of Ketones

✍ Scribed by Rocío Marcos; Ciril Jimeno; Miquel A. Pericàs

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 339 KB
Volume: 353
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.201000948

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✦ Synopsis

Chlorosulfonylated polystyrene, a commodity resin, reacts with enantiopure 1,2-diamines to afford, in a single step, high loading catalytic resins involving monosulfonylated 1,2-diamino moieties. These functional polymers form stable (p-cymene)ruthenium chloride [RuClA C H T U N G T R E N N U N G (p-cymene)] complexes that efficiently catalyze (down to S/C = 150) the asymmetric transfer hydrogenation (ATH) of alkyl aryl ketones with formic acid-triethylamine under essential-ly solvent-free (down to 0.25 mL mmol À1 ) reaction conditions. Among these resins, the immobilized version of TsDPEN stands out as a most practical catalyst for ATH: Uniformly high enantioselectivities are achieved with its use at low catalyst loading, and the resin can be recycled with virtually no limits.

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