Solvent-dependent stereoselectivity in a Still-Wittig rearrangement: an experimental and ab initio study.
Solvent-dependent stereoselectivity in a Still-Wittig rearrangement: an experimental and ab initio study.
复制标题
Still-Wittig 重排中溶剂依赖性立体选择性：实验和从头开始研究。
DOI：
10.1021/ol015764d
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发表时间：
2001
期刊：
影响因子：
5.2
通讯作者：
Etzkorn,FA
中科院分区：
文献类型：
--
作者：
Hart,SA;Trindle,CO;Etzkorn,FA
The Still−Wittig rearrangement gave opposite selectivities for (Z:E)-alkenes in THF (3:1) vs toluene (1:3) in the synthesis of serine−proline dipeptide amide isosteres. Four transition states leading to (Z)-and (E)-alkenes with THF and without (representing toluene) were identified by ab initio calculations at the 3-21G* level. The calculated (Z:E)-ratios with THF (4.7:1) and without THF (1:3.2) suggested that the transition state geometries and energies were well-represented by the calculations.
