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Title: Synthesis of novel cinchona-amino acid hybrid organocatalysts for asymmetric catalysis
Authors: Burke, Anthony
Barrulas, Pedro
Benaglia, Maurizio
Editors: Da, Stephen
Keywords: Organocatálise
Issue Date: 30-Jun-2014
Publisher: Elsevier
Abstract: Three novel subclasses of cinchonidine derivatives coupled to diverse amino acids were prepared in very good overall yield and tested in a benchmark organocatalytic aldol reaction, between acetone and aromatic aldehydes. These subclasses are a family of amino acid-cinchonidine (subclass A), N-formamides-cinchonidine (subclass B) and dipeptide-cinchonidine (subclass C) hybrids. Our main goal, besides obtaining very good yields and enantioselectivities, was to understand the influence of the amino acid side chain residues on the enantioselectivity of the asymmetric aldol reactions. Different amino acid tethered cinchonidine hybrids were compared and their catalytic behaviour was evaluated, allowing good enantioselectivities to be achieved, 92% ee in one case. Other reactions such as Biginelli, Michael addition and ketimine hydrosilylation reactions were screened with these ligands, but the outcome was less successful
ISSN: 0957-4166
Type: article
Appears in Collections:QUI - Publicações - Artigos em Revistas Internacionais Com Arbitragem Científica

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