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

被引：1

作者：

Felix, Ana Rita G. ^{[1
]}

Simoes, Pedro R. D. ^{[1
]}

Sousa, Francisco J. P. M. ^{[1
]}

Silva Serra, M. Elisa ^{[1
]}

Murtinho, Dina ^{[1
]}

机构：

[1] Univ Coimbra, Dept Chem, CQC, Coimbra, Portugal

来源：

LETTERS IN ORGANIC CHEMISTRY | 2020年 / 17卷 / 05期

关键词：

Thiazolidines; organocatalyst; aldol reaction; enantioselective; asymmetric synthesis; additives; L-PROLINE; CATALYSTS; PROLINAMIDES; THIOUREAS; WATER;

D O I：

10.2174/2210681209666190807155816

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：372 / 380

页数：9

共 48 条

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