Novel chiral bifunctional l-thiazoline-amide derivatives: design and application in the direct enantioselective aldol reactions |
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Authors: | Zhiyong Gong Chiyu Wei Ye Shi Qingchuan Zheng Zhiguang Song Zaiqun Liu |
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Affiliation: | 1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China;2. State Key Laboratory of Theoretical and Computational Chemistry, Changchun 130023, PR China |
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Abstract: | Several novel chiral bifunctional l-thiazoline-amide derivatives were simply synthesized from commercially available l-cysteine and l-proline in high yield. These catalysts were subsequently applied to the direct enantioselective aldol reactions of various aldehydes, which are rarely reported in the literature. The products with anti configuration were obtained up to 97% ee and 99% dr when the l-thiazoline-amide derivatives were used. A plausible transition state model was proposed to explain the observed enantio and diastereoselectivities. |
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Keywords: | Chiral catalyst Asymmetric direct aldol reactions l-Thiazoline-amide |
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