Pd-Catalyzed asymmetric [5 + 2] cycloaddition of vinylethylene carbonates and cyclic imines: access to N-fused 1,3-oxazepines,Organic & Biomolecular Chemistry

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Pd-Catalyzed asymmetric [5 + 2] cycloaddition of vinylethylene carbonates and cyclic imines: access to N-fused 1,3-oxazepines
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-11-23 , DOI: 10.1039/d0ob02159h
Hye-In Ahn ₁ , Jong-Un Park , Zi Xuan , Ju Hyun Kim

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A Pd-catalyzed asymmetric [5 + 2] cycloaddition reaction was developed for the synthesis of N-fused 1,3-oxazepines using vinylethylene carbonates and sulfamate-derived cyclic imines. Under mild reaction conditions, a series of optically active N-fused 1,3-oxazepines were synthesized in good yields (up to 89%) and enantioselectivities (up to 90 : 10 er), indicating this method as a straightforward approach to enantiomerically enriched 1,3-oxazepine derivatives. The synthetic utility of the presented reaction was further demonstrated by the successful transformation of the resulting 1,3-oxazepines to useful polycyclic N-fused 1,3-oxazepanes.

中文翻译：

Pd催化的乙烯基碳酸亚乙酯和环状亚胺的不对称[5 + 2]环加成：获得N-稠合1,3-氧氮杂卓

开发了一种 Pd 催化的不对称 [5 + 2] 环加成反应，用于使用乙烯基碳酸亚乙酯和氨基磺酸酯衍生的环状亚胺合成N-稠合 1,3-恶氮杂。在温和的反应条件下，以良好的收率（高达 89%）和对映选择性（高达 90 : 10 er）合成了一系列具有光学活性的N-稠合 1,3-氧氮杂卓，表明该方法是一种直接富集对映体的方法1,3-氧氮杂卓衍生物。将所得 1,3-氧氮杂卓成功转化为有用的多环N-稠合 1,3-氧氮杂卓，进一步证明了所提出反应的合成效用。

更新日期：2020-11-27

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