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首页> 外文期刊>Chemistry: A European journal >A Substrate-Based Approach to Skeletal Diversity from Dicobalt Hexacarbonyl (C1)-Alkynyl Glycals by Exploiting Its Combined Ferrier–Nicholas Reactivity
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A Substrate-Based Approach to Skeletal Diversity from Dicobalt Hexacarbonyl (C1)-Alkynyl Glycals by Exploiting Its Combined Ferrier–Nicholas Reactivity

机译：基于底物的二钴六羰基（C1）-炔基二元醇通过利用其结合的费-尼古拉斯反应性来进行骨骼多样性的方法

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摘要

Novel substrates that combine dicobalt hexacarbonyl propargyl (Nicholas) and pyranose-derived allylic (Ferrier) cations have been generated by treatment of hexacarbonyldicobalt (C-1)-alkynyl glycals with BF_3?Et_2O. The study of these cations has resulted in the discovery of novel reaction pathways that have shown to be associated to the nature of O-6 substituent in the starting alkynyl glycals. Accordingly, compounds resulting from ring expansion (oxepanes), ring contraction (tetrahydrofurans), or branched pyranoses, by incorporation of nucleophiles, can be obtained from 6-O-benzyl, 6-hydroxy, or 6-O-silyl derivatives, respectively. The use of a 6-O-allyl alkynyl glycal led to a suitable funtionalized oxepane able to experience an intramolecular Pauson–Khand cyclization leading to a single tricyclic derivative.
机译：通过用BF_3→Et_2O处理六羰基二钴（C-1）-炔基糖，已经产生了将二钴二羰基六羰基炔丙基（Nicholas）和吡喃糖衍生的烯丙基（Ferrier）阳离子结合的新型底物。对这些阳离子的研究导致发现了新的反应途径，这些反应途径与起始炔基糖基中的O-6取代基的性质有关。因此，通过并入亲核试剂，由环膨胀（氧杂环丁烷），环收缩（四氢呋喃）或支链吡喃酶产生的化合物可以分别从6-O-苄基，6-羟基或6-O-甲硅烷基衍生物获得。使用6-O-烯丙基炔基缩醛可以产生合适的官能化氧杂环丁烷，能够经历分子内的Pauson-Khand环化反应，从而生成单个三环衍生物。

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