Diversity-Oriented Synthesis of Oxacyclic Spirooxindole Derivatives through Ring-Closing Enyne Metathesis and Intramolecular Pauson–Khand (2+2+1) Cyclization of Oxindole Enynes,Advanced Synthesis & Catalysis

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Diversity-Oriented Synthesis of Oxacyclic Spirooxindole Derivatives through Ring-Closing Enyne Metathesis and Intramolecular Pauson–Khand (2+2+1) Cyclization of Oxindole Enynes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-09-14 04:51:34 , DOI: 10.1002/adsc.201700511
Satheeshkumar Reddy Kandimalla _{1,

2} , Gowravaram Sabitha _{1,

2}

Affiliation

An efficient approach for a reagent-based diversity-oriented synthesis (DOS) of novel fused spirooxindole scaffolds from oxindole enynes has been developed. The reaction involves a metal-catalyzed C-3 allylation/vinylation/homoallylation of N-substituted isatins which gives rise to the corresponding alcohols that can be converted into the required enynes. Further transformation to diverse complex molecular scaffolds proceeds via a subsequent ruthenium-catalyzed ring-closing enyne metathesis (RCEYM), or cobalt-catalyzed intramolecular Pauson–Khand (2+2+1) cyclization reaction (IPKR). This strategy provides a facile approach to various spirooxindole-vinyldihydropyrans/tetrahydrooxepines and spirocyclic fused cyclopentenones in good to excellent yields.

中文翻译：

闭环烯炔的复分解和羟吲哚烯炔的分子内Pauson-Khand（2 + 2 + 1）环化反应，以多样性为导向的合成氧杂环螺氧杂吲哚衍生物

已经开发了一种有效的方法，用于基于试剂的来自羟吲哚烯炔的新型稠合螺氧杂吲哚支架的定向合成（DOS）。该反应涉及N-取代的靛红的金属催化的C-3烯丙基化/乙烯基化/均烯丙基化，这产生了可以转化为所需烯炔的相应的醇。通过随后的钌催化的闭环烯炔复分解（RCEYM）或钴催化的分子内Pauson–Khand（2 + 2 + 1）环化反应（IPKR），可以进一步转化为各种复杂的分子支架。该策略为各种螺环吲哚-乙烯基二氢吡喃/四氢氧杂环丁烷和螺环稠合的环戊烯酮提供了简便的方法，收率良好。

更新日期：2017-09-14

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