Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction):: scope and asymmetric applications
Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction):: scope and asymmetric applications
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DOI：
10.1039/b316502g
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发表时间：
2004-01-01
影响因子：
3.2
通讯作者：
Yokochi, AFT
中科院分区：
文献类型：
--
作者：
Bourland, TC;Carter, RG;Yokochi, AFT
发展了一种钒催化的前手性芳基、烯丙基硒化合物的氧化-串联[2，3]Sigmatroic重排的方法。该方案已经在一系列底物上进行了筛选，以测试其通用性和有效性。在一系列具有非对映异构体比(D.R.)的手性恶唑类化合物上，研究了该方法在合成富含对映异构体的烯丙醇中的适用性。在烯丙醇产品中观察到的手性转移是净1，9-和/或1，10-诱导的结果。最后，通过X射线晶体分析，观察到了含恶唑的硒化物中的第一个硒-氧非键相互作用的例子。
A vanadium-catalyzed method for the oxidation of prochiral aryl, allylic selenides with tandem [2,3] sigmatropic rearrangement has been developed. This protocol has been screened on a series of substrates to test for its generality and effectiveness. The applicability of this methodology to the synthesis of enantiomerically enriched allylic alcohols has been studied on a series of chiral oxazole-containing systems with a diastereomeric ratio (d.r.) of up to 85 : 15. The chiral transfer observed in the allyl alcohol products is the result of a net 1,9- and/or 1,10-induction. Finally, the first example of a selenium-oxygen nonbonding interaction in oxazole-containing selenide appears to have been observed via X-ray crystal analysis.