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Reverse-docking study of the organocatalyzed asymmetric Strecker hydrocyanation of aldimines and ketimines

zhangshoude 添加于 2009-9-25 11:27 | 1764 次阅读 | 0 个评论

作者
Joseph Harriman D, Deleavey GF, Lambropoulos A, Deslongchamps G
摘要
A methodology for reverse-docking flexible organocatalysts to rigid transition state models of catalyst-free asymmetric reactions has been developed. The investigation of Jacobsen's chiral thiourea-based organocatalyst for the hydrocyanation of aldimines and ketimines (Strecker reaction) via reverse-docking is described. Results from reverse-docking Jacobsen's organocatalyst to both enantiomers of six Strecker TS-models (i.e., rigid transition state models of the catalyst-free asymmetric reaction) indicate a clear energetic preference for binding the organocatalyst to the R -enantiomer TS-model, which is in agreement with experimental results. The most favorable docking poses reveal structural features consistent with principles of molecular recognition, catalysis, and NMR data. These poses may represent simplified geometric models of the transition state for the catalyzed reaction.
详细资料
- 文献种类:期刊
- 期刊名称: Tetrahedron
- 期刊缩写: Tetrahedron
- 期卷页: 2007年第63卷第52期 13032-13038页
- ISBN: 0040-4020
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