2,3-Epoxyamide-alcohols in Domino Reactions: En Route to Molecular Diversity

IF 2.5 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Dr. Abderrahman El Bouakher, Dr. Jérôme Lhoste, Prof. Arnaud Martel, Dr. Sébastien Comesse
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Abstract

The synthesis of polycyclic γ- and δ-lactams bearing up to four contiguous fully controlled stereocenters is presented. For that purpose, we developed an original approach based on the use of 2,3-epoxyamides in domino reactions by taking advantage of the nucleophilic nitrogen atom and electrophilic epoxide. In reaction with enol ethers bearing gem bis-electrophiles on the double bond as Michael acceptors, four different reaction pathways were observed. They all started with a domino oxa-Michael/aza-Michael/epoxide opening sequence and depending on substrates engaged could be followed either by a lactonization or a hemiketalization/retro-aldol cascade. Thus, four original fully-substituted piperidine- or pyrrolidine-2-one scaffolds were selectively synthesized in good to high yields. Moreover, these polycyclic lactams were obtained in high stereo- and chemo-selectively highlighting the efficiency and molecular diversity offered by this new methodology that should offer various synthetic opportunities in the future.

Abstract Image

Abstract Image

多米诺反应中的 2,3-环氧酰胺醇:分子多样性之路。
本文介绍了具有最多四个连续完全受控立体中心的多环γ-和δ-内酰胺的合成。为此,我们开发了一种基于 2,3-环氧酰胺多米诺反应的原创方法,利用亲核氮原子和亲电环氧化物的优势。在与双键上带有双亲电性的烯醇醚作为迈克尔受体进行反应时,观察到了四种不同的反应途径。它们都以多米诺 oxa-Michael/aza-Michael/epoxide 开启顺序为起点,并根据参与反应的底物的不同,可进行内酯化或半金属化/反醛化级联反应。因此,四种原始的全取代哌啶或吡咯烷-2-酮支架被选择性地合成出来,而且产量很高。此外,这些多环内酰胺具有很高的立体选择性和化学选择性,突出了这种新方法的高效性和分子多样性,为未来提供了各种合成机会。
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来源期刊
ChemistryOpen
ChemistryOpen CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.80
自引率
4.30%
发文量
143
审稿时长
1 months
期刊介绍: ChemistryOpen is a multidisciplinary, gold-road open-access, international forum for the publication of outstanding Reviews, Full Papers, and Communications from all areas of chemistry and related fields. It is co-owned by 16 continental European Chemical Societies, who have banded together in the alliance called ChemPubSoc Europe for the purpose of publishing high-quality journals in the field of chemistry and its border disciplines. As some of the governments of the countries represented in ChemPubSoc Europe have strongly recommended that the research conducted with their funding is freely accessible for all readers (Open Access), ChemPubSoc Europe was concerned that no journal for which the ethical standards were monitored by a chemical society was available for such papers. ChemistryOpen fills this gap.
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