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Title: Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions
Authors: Félix, Ana Rita G.
Simões, Pedro R. D. 
Sousa, Francisco J. P. M.
Serra, Maria Elisa Silva 
Murtinho, Dina 
Keywords: Thiazolidines; Organocatalyst; Aldol reaction; Enantioselective; Asymmetric synthesis; Additives
Issue Date: 2020
Publisher: Bentham Science Publishers
Project: info:eu-repo/grantAgreement/FCT/00313/2019/PT 
Serial title, monograph or event: Letters in Organic Chemistry
Volume: 17
Issue: 5
Abstract: Several novel chiral organocatalysts derived from thiazolidines containing amide and thioureia functionalities were synthesized in good yields. These organocatalysts were tested in the asymmetric aldol reaction of acetone with p-nitrobenzaldehyde. Reaction parameters such as reaction time, catalyst loading and solvent were optimized. Products with conversions up to 84% and enantiomeric ratios (er) up to 84.5:15.5 (R:S) were obtained. The effect of several chiral and non-chiral additives on the reactivity and selectivity of the reaction was also evaluated. The reaction was extended to other aromatic aldehydes with the best organocatalyst and when p-bromobenzaldehyde was used, an er of 94.5:5.5 (R:S) was obtained.
ISSN: 15701786
DOI: 10.2174/2210681209666190807155816
Rights: embargoedAccess
Appears in Collections:I&D CQC - Artigos em Revistas Internacionais

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