Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions

Author(s): Ana Rita G. Félix, Pedro R.D. Simões, Francisco J.P.M. Sousa, M. Elisa Silva Serra, Dina Murtinho*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 5 , 2020

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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.

Keywords: Thiazolidines, organocatalyst, aldol reaction, enantioselective, asymmetric synthesis, additives.

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VOLUME: 17
ISSUE: 5
Year: 2020
Page: [372 - 380]
Pages: 9
DOI: 10.2174/2210681209666190807155816
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