甘氨酸席夫碱手性Ni(II)配合物平台上的醛醇加成-环化反应级联

Ukr. Bioorg. Acta 2021, Vol. 16, N1 Pub Date : 2021-06-30 DOI:10.15407/bioorganica2021.01.003

Yupiao Zou, Zizhen Yin, Haibo Mei, H. Konno, H. Moriwaki, V. Soloshonok, Jianlin Han

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引用次数: 1

摘要

以新型甘氨酸席夫碱手性Ni(II)配合物为平台，设计加成-环化反应级联，探讨相应的(S)(2S,3S)/(S)(2S,3R)非对映体的动力学/热力学生成。结果表明，由于可逆醛醇加成的速率大大高于随后的环化步骤，最终的内酯产物反映了热力学立体控制。新型(S)-Ni(II)配合物反应的非对映选择性为4/1 (S)(2S,3S)/(S)(2S,3R)，比之前报道的1.7/1的比例有所提高。

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Aldol Addition-Cyclization Reaction Cascade on a Platform of Chiral Ni(II) Complex of Glycine Schiff Base

Using platform of a new type of chiral Ni(II) complex of glycine Schiff base we designed addition-cyclization reaction cascade to explore aspects of kinetic/thermodynamic formation of the corresponding (S)(2S,3S)/(S)(2S,3R) diastereomers. It was found that the final lactone products reflect the thermodynamic stereocontrol due to much greater rates of the reversible aldol addition vs. subsequent cyclization step. The observed 4/1 (S)(2S,3S)/(S)(2S,3R) diastereoselectivity in the reactions of new type of (S)-Ni(II) complexes constitute an improvement over the previously reported 1.7/1 ratio.

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Ukr. Bioorg. Acta 2021, Vol. 16, N1

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