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Literature DB >> 26504516

Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases.

Maximilian Tiffner¹, Johanna Novacek¹, Alfonso Busillo², Katharina Gratzer¹, Antonio Massa², Mario Waser¹.

Abstract

Bifunctional chiral urea-containing quaternary ammonium salts can be straightforwardly synthesised in good yield and with high structural diversity via a scalable and operationally simple highly telescoped sequence starting from trans-1,2-cyclohexanediamine. These novel hybrid catalysts were systematically investigated for their potential to control glycine Schiff bases in asymmetric addition reactions. It was found that Michael addition reactions and the herein presented aldol-initiated cascade reaction can be carried out to provide enantiomeric ratios up to 95 : 5 and good yields under mild conditions at room temperature.

Entities: Chemical

Year: 2015 PMID： 26504516 PMCID： PMC4618300 DOI： 10.1039/C5RA14466C

Source DB: PubMed Journal: RSC Adv ISSN： 2046-2069 Impact factor: 3.361

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