Synthesis of vicinal amino alcohols via a tandem acylnitrene aziridination-aziridine ring opening
Synthesis of vicinal amino alcohols via a tandem acylnitrene aziridination-aziridine ring opening
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DOI：
10.1021/jo970473x
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发表时间：
1997-06-27
影响因子：
3.6
通讯作者：
Stanchina, DM
中科院分区：
文献类型：
--
作者：
Bergmeier, SC;Stanchina, DM
报道了不同取代的邻位氨基醇的简便合成方法。我们已经证明，这些氨基醇可以很容易地从恶唑烷酮与碱水溶液处理制备。我们已经合成了各种取代的双环氮丙啶前体从相应的叠氮甲酸酯使用分子内的氮丙啶化反应。这些双环氮丙啶的亲核开环使用碳，氧，氮，硫，和卤素的亲核试剂提供恶唑烷酮在良好的产率和高的区域选择性。在所有情况下，亲核攻击只发生在氮丙啶环的最少取代的碳上。因此，我们的方法允许方便和快速地获得邻位氨基醇功能，这是许多天然产物的重要结构组分。
A facile synthesis of differently substituted vicinal amino alcohols is reported. We have demonstrated that these amino alcohols could be readily prepared from the oxazolidinones by treatment with aqueous base. We have synthesized a variety of substituted bicyclic aziridine precursors from the corresponding azidoformates using an intramolecular aziridination reaction. The nucleophilic ring opening of these bicyclic aziridines using carbon, oxygen, nitrogen, sulfur, and halogen-containing nucleophiles provided the oxazolidinones in good yield with high regioselectivity. In all cases, nucleophilic attack occurred exclusively at the least substituted carbon of the aziridine ring. Consequently, our approach allows for convenient and rapid access to the vicinal amino alcohol functionality, an important structural component of many natural products.