Staudinger reactions of unsymmetrical cyclic ketenes: a synthetically useful approach to spiro β-lactams and derivatives. Reaction mechanism and theoretical studies

Eduardo Alonso Carlos del Pozo and Javier González

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Staudinger reactions of unsymmetrical cyclic ketenes: a synthetically useful approach to spiro β-lactams and derivatives. Reaction mechanism and theoretical studies

机译：不对称环状烯酮的斯托丁格反应：一种合成有用的方法，用于合成螺旋β-内酰胺及其衍生物。反应机理与理论研究

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An efficient and operationally simple synthesis of tetrahydrofuran-derived spiro-β-lactams using the ketene–iminencycloaddition route is described. Also the preparation of spiro-N-sulfonyl-β-lactam derivatives, which are analogsnof monobactams, is reported. As far as we know, this is the first time that an unsymmetrical cyclic ketene is used inna Staudinger-type reaction. The experimental evidence suggests the involvement of a ketene derived from the acylnchloride precursor in the reaction. High-level ab initio calculations have been performed in order to get insight intonthe electronic effects controlling the stereochemical outcome of the reactions.

机译：描述了一种使用烯酮-亚胺环加成法高效，简单地合成四氢呋喃衍生的螺-β-内酰胺的方法。还报道了螺-N-磺酰基-β-内酰胺衍生物的制备，其是单bactams的类似物。据我们所知，这是在Staudinger型反应中首次使用不对称环状烯酮。实验证据表明，衍生自酰氯前体的乙烯酮参与了反应。为了从控制反应的立体化学结果的电子效应中获得洞察力，已经进行了高级的从头算。

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《Journal of the Chemical Society, Perkin Transactions 1》 |2002年第4期|p.571-576|共6页
作者
Eduardo Alonso Carlos del Pozo and Javier González;
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作者单位

Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, 33071 Oviedo, Spain.E-mail: FJGF@sauron.quimica.uniovi.es;

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1. Staudinger reactions of unsymmetrical cyclic ketenes: a synthetically useful approach to spiro beta-lactams and derivatives. Reaction mechanism and theoretical studies [J] . Alonso E., del Pozo C., Gonzalez J. Journal of the Chemical Society, Perkin Transactions 1 . 2002,第4期

机译：不对称环状烯酮的斯托丁格反应：螺旋β-内酰胺及其衍生物的合成有用方法。反应机理与理论研究
2. Diastereoselective Synthesis of Highly Constrained Spiro-P-Lactams by the Staudinger Reaction Using an Unsymmetrical Bicyclic Ketene [J] . Andrea Trabocchi, Claudia Lalli, Francesco Guarna European journal of organic chemistry . 2007,第27期

机译：非对称双环丁烯的斯托丁格反应非对映选择性合成高度约束的螺-P-内酰胺
3. Diastereoselective [2+2]-cycloaddition reactions of unsymmetrical cyclic ketenes with imines: Synthesis of modified prolines and theoretical study of the reaction mechanism [J] . Macias A, Alonso E, del Pozo C, The Journal of Organic Chemistry . 2004,第21期

机译：不对称环状烯酮与亚胺的非对映选择性[2 + 2]-环加成反应：修饰脯氨酸的合成及反应机理的理论研究
4. A Theoretical Study on the Mechanism of Dimerization Reactions of Ketene [C] . ZHANG ZHIGUO, HU KAITANG 第二届国际造纸与环境学术会议（The Second International Papermaking Environment Conference）论文集 . 2008

机译：乙烯酮二聚反应机理的理论研究
5. Theoretical study of the mechanisms for epoxidation and ketene addition reactions of strained cyclic olefins. [D] . Chamras, Sevada Andranik. 2001

机译：应变环烯烃环氧化和乙烯酮加成反应机理的理论研究。
6. Enantioselective Nucleophilic Catalysis: The Synthesis of Aza-β-Lactams via 2+2 Reactions of Ketenes with Azo Compounds [O] . Jacob M. Berlin, Gregory C. Fu -1

机译：对映选择性亲核催化：通过酮丁酮与偶氮化合物的2 + 2反应合成Aza-β-内酰胺
7. Diastereoselective 2+2-Cycloaddition Reactions of Unsymmetrical Cyclic Ketenes with Imines: Synthesis of Modified Prolines and Theoretical Study of the Reaction Mechanism [O] . -1

机译：非对称环形烯烯酮与亚胺的非对映选择性2 + 2-环加成反应：改性脯氨酸的合成和反应机制的理论研究

Staudinger reactions of unsymmetrical cyclic ketenes: a synthetically useful approach to spiro β-lactams and derivatives. Reaction mechanism and theoretical studies

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