Chiral nonracemic pyridine thiols and thioethers applied in palladium-catalyzed allylic substitution. An example of near-perfect enantioselection
Chiral nonracemic pyridine thiols and thioethers applied in palladium-catalyzed allylic substitution. An example of near-perfect enantioselection
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手性非外消旋吡啶硫醇和硫醚应用于钯催化烯丙基取代。
DOI：
10.1021/jo9806299
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发表时间：
1998
影响因子：
3.6
通讯作者：
R. Kellogg
中科院分区：
文献类型：
--
作者：
B. Koning;A. Meetsma;R. Kellogg
以2,6-鲁替丁与硫芬酮碱诱导加成的方法合成了吡啶硫醇和二硫醇。这些硫醇通过烷基化转化为它们的硫醚衍生物。这些化合物应用于钯催化的1,3-二苯丙-2-烯基乙酸酯的烯丙基取代，得到了几乎绝对的对映体过量（98%）和高化学收率（96%）。钯烯丙基中间体的分离对这些体系的手性识别的起源有了深入的了解。
Pyridine thiols and dithiols have been synthesized by base-induced addition of 2,6-lutidine to thiofenchone. These thiols were converted to their thioether derivatives by alkylation. Application of these compounds in palladium-catalyzed allylic substitution on 1,3-diphenylprop-2-enyl acetate gave nearly absolute enantiomeric excess (98%) and high chemical yield (96%). Isolation of a palladium allylic intermediate gave insight in the origin of chiral recognition for these systems.