ArticleJournal of the American Chemical Society2010
Enantiomerically pure trans-beta-lactams from alpha-amino acids via compact fluorescent light (CFL) continuous-flow photolysis.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Carbene-Ketene Formal [3 + 2] Cycloaddition Enabled by Visible-Light-Induced Dual Photolysis of Diazo Compounds.JACS Au · 2026Article
- Visible light-induced 1,2-alkoxy shift of α-diazoacetates for Wolff rearrangements - access to oxyketenes.Chemical science · 2026Article
- Synthesis, Computational Studies, and Structural Analysis of 1-(3,5-Dimethoxyphenyl)azetidin-2-ones with Antiproliferative Activity in Breast Cancer and Chemoresistant Colon Cancer.Pharmaceuticals (Basel, Switzerland) · 2025Article
- Expanding the Chemical Space of Electrophilic β-Glycosyl β-Lactams through Photoinduced Diastereoselective Functionalization.Organic letters · 2024Article
- Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.Chemical reviews · 2024Review
- Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles.Beilstein journal of organic chemistry · 2024Article
- Copper-Catalyzed Enantioconvergent Radical C(spPrecision chemistry · 2023Article
- Photo-Flow Technology for Chemical Rearrangements: A Powerful Tool to Generate Pharmaceutically Relevant Compounds.ACS medicinal chemistry letters · 2023Article
- Synthesis, Characterisation and Mechanism of Action of Anticancer 3-Fluoroazetidin-2-ones.Pharmaceuticals (Basel, Switzerland) · 2022Article
- Into the Blue: Ketene Multicomponent Reactions under Visible Light.The Journal of organic chemistry · 2021Article
- Stoichiometric Photochemical Carbene Transfer by Bamford-Stevens Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Recent Advances in Enantioselective Photochemical Reactions of Stabilized Diazo Compounds.Molecules (Basel, Switzerland) · 2019Review
- Blue light-promoted photolysis of aryldiazoacetates.Chemical science · 2018Article
- Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides.Beilstein journal of organic chemistry · 2018Article
- Synthetic Approaches toward Monocyclic 3-Amino-β-lactams.ChemistryOpen · 2017Review
- Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions.Chemical science · 2016Article
- EnantioselectiveChemical science · 2015Article
- π-π interaction energies as determinants of the photodimerization of mono-, di-, and triazastilbenes.The Journal of organic chemistry · 2014Article
- Flow photochemistry: Old light through new windows.Beilstein journal of organic chemistry · 2012Article
- Photochemistry with laser radiation in condensed phase using miniaturized photoreactors.Beilstein journal of organic chemistry · 2012Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Photolysis of alpha-diazo-N-methoxy-N-methyl (Weinreb) beta-ketoamides derived from enantiomerically pure (EP) alpha-amino acids affords the corresponding EP beta-lactams via an intramolecular Wolff rearrangement. The photochemistry is promoted with either standard UV irradiation or through the use of a 100 W compact fluorescent light; the latter affords a safe and environmentally friendly alternative to standard photolysis conditions. A continuous-flow photochemical reactor made from inexpensive laboratory equipment reduced reaction times and was amenable to scale-up. The diastereoselectivity (cis or trans) of the product beta-lactams has been shown to vary from modest to nearly complete. An extremely facile, atom-economical method for the epimerization of the product mixture to the trans isomer, which is generally highly crystalline, has been developed. Evidence for C3 epimerization of Weinreb amide structures via a nonbasic, purely thermal route is presented. Subsequent transformations of both the Weinreb amide at C3 (beta-lactam numbering) and the amino acid side chain at C4 are well-tolerated, allowing for a versatile approach to diverse beta-lactam structures. The technology is showcased in the synthesis of a common intermediate used toward several carbapenem-derived structures starting from unfunctionalized aspartic acid.
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