Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water | Zendy

Elif Keskin | Zendy; Çiğdem Yolaçan | Zendy; Feray Aydoğan | Zendy

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Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water

Author(s) -

Elif Keskin,

Çiğdem Yolaçan,

Feray Aydoğan

Publication year - 2020

Publication title -

acta chimica slovenica

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.289

H-Index - 46

eISSN - 1580-3155

pISSN - 1318-0207

DOI - 10.17344/acsi.2018.4748

Subject(s) - aldol reaction , chemistry , benzoic acid , pyrrolidine , organocatalysis , proline , catalysis , organic chemistry , reaction conditions , enantioselective synthesis , amino acid , biochemistry

New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0 °C in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed.

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