Formal [4 + 2] Cycloadditions of Anhydrides and α,β-Unsaturated N-Tosyl Ketimines,Organic Letters

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Formal [4 + 2] Cycloadditions of Anhydrides and α,β-Unsaturated N-Tosyl Ketimines
Organic Letters ( IF 4.9 ) Pub Date : 2019-02-05 00:00:00 , DOI: 10.1021/acs.orglett.8b04091
Noah P. Burlow ₁ , Sara Y. Howard ₁ , Carla M. Saunders ₁ , James C. Fettinger ₁ , Dean J. Tantillo ₁ , Jared T. Shaw ₁

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A method for the diastereoselective synthesis of highly substituted β-enamino ketones from anhydrides and ketone-derived imines is reported. Cyclic, enolizable anhydrides undergo a base-promoted conjugate addition reaction with α,β-unsaturated N-tosyl ketimines, followed by an intramolecular acylation to give formal [4 + 2] cycloaddition products. The carboxylic acid-containing products are formed with modest selectivity for the cis-diastereomer and can be fully epimerized to the trans-diastereomer upon esterification.

中文翻译：

酸酐与α，β-不饱和N-甲苯磺酰基酮亚胺的形式[4 + 2]的环加成反应

报道了一种由酸酐和酮衍生的亚胺非对映选择性合成高度取代的β-烯胺酮的方法。环状可烯醇化酸酐与α，β-不饱和N-甲苯磺酰基酮亚胺进行碱促进的共轭加成反应，然后进行分子内酰化，得到正式的[4 + 2]环加成产物。所形成的含羧酸的产物对顺式-非对映异构体具有适度的选择性，并且在酯化后可以完全差向异构为反式-非对映异构体。

更新日期：2019-02-05

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