Synthesis of Spirocyclic Isoindolones Using an Alkynyl aza-Prins/Oxidative halo-Nazarov Cyclization Sequence.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c00191
Abstract: In this report, we describe an alkynyl halo-aza-Prins cyclization of 3-hydroxyisoindolones to prepare aza-Prins products. These Prins adducts undergo oxidation at the 3-isoindolone position after activation of the amide by triflic anhydride and 2-chloropyridine to… read more here.
Keywords: nazarov cyclization; aza prins; halo nazarov; halo ... See more keywords
Domino Semipinacol/Iterative Aldol/Iso-Nazarov Cyclization to Triaryl-cyclopentenone: Enantioselective Synthesis of Combretastatin A-4 Analogues.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01531
Abstract: A facile domino strategy has been developed for the synthesis of a biologically active cyclopent-2-enone core containing combretastatin A-4 (CA-4) analogues from aryloxirane and aryl aldehyde. This one-pot method involves a sequence of semipinacol rearrangement,… read more here.
Keywords: nazarov cyclization; enantioselective synthesis; iterative aldol; combretastatin analogues ... See more keywords
Benzyne Polyfunctionalization via a Tandem C-C σ-Bond Insertion and Photo-Nazarov Cyclization.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02652
Abstract: A tandem benzyne C-C σ-bond insertion reaction and photo-Nazarov cyclization protocol was developed, leading to the formation of three C-C bonds at consecutive positions of a benzene ring with concomitant assembly of a 6-5-6 tricyclic… read more here.
Keywords: bond insertion; photo nazarov; nazarov cyclization;
Oxa-Nazarov Cyclization-Michael Addition Sequence for the Rapid Construction of Dihydrofuranones.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03601
Abstract: The Nazarov cyclization has been established as a powerful tool in constructing cyclopentenone skeletons. In sharp contrast, oxa-Nazarov cyclization that affords dihydrofuranones, a new type of product, has been less explored. In this work, we… read more here.
Keywords: nazarov cyclization; oxa nazarov; michael addition; cyclization ... See more keywords
Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (-)-Englerin A.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.7b02428
Abstract: A divergent entry to the chiral bicyclo[5.3.0]decane skeletons relevant to sesqui- and higher terpenoids has been achieved. Its usefulness was demonstrated by formal synthesis of a guaiane sesquiterpenoid (-)-englerin A. The key reactions are (i)… read more here.
Keywords: bicyclo; formal synthesis; chiral bicyclo; nazarov cyclization ... See more keywords
Nickel/Copper Dual Catalysis for Sequential Nazarov Cyclization/Decarboxylative Aldol Reaction.
Sign Up to like & getrecommendations! Published in 2018 at "Organic letters"
DOI: 10.1021/acs.orglett.8b02426
Abstract: A nickel/copper cocatalyzed sequential Nazarov cyclization/decarboxylative aldol reaction is reported. Various β-hydroxycyclopentenones containing three contiguous stereocenters were prepared in good yields with high diastereoselectivities. A gram-scale reaction and further derivatizations were easily achieved to highlight… read more here.
Keywords: decarboxylative aldol; nickel copper; nazarov cyclization; cyclization decarboxylative ... See more keywords
Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones
Sign Up to like & getrecommendations! Published in 2019 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.8b13899
Abstract: We report a catalytic asymmetric Nazarov cyclization of simple, acylic, alkyl-substituted divinyl ketones using our recently disclosed strong and confined imidodiphosphorimidate Brønsted acids. The corresponding monocyclic cyclopentenones are formed in good yields and excellent regio-,… read more here.
Keywords: strong confined; divinyl ketones; nazarov cyclization; cyclization simple ... See more keywords
Asymmetric binary-acid catalysis: a diastereo- and enantioselective oxa-Nazarov cyclization-Michael addition of conjugated 1,2-diketones
Sign Up to like & getrecommendations! Published in 2023 at "Organic Chemistry Frontiers"
DOI: 10.1039/d3qo00558e
Abstract: Diastereo- and enantioselective oxa-Nazarov cyclization-Michael addition of conjugated 1,2-diketones was achieved by using an asymmetric binary-acid catalysis with chiral phosphoric acid and FeBr3. The reaction affords the corresponding chiral 3(2H)-furanones... read more here.
Keywords: nazarov cyclization; enantioselective oxa; diastereo enantioselective; oxa nazarov ... See more keywords
Catalyst-Free Regioselective Nazarov Cyclization of Aryl Allenyl Ketones
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DOI: 10.1055/s-0036-1591487
Abstract: The catalyst-free Nazarov cyclization of aryl allenyl ketones under thermal condition is developed. Various densely functionalized 2,3-dihydroindanones or indenones are readily produced in moderate to excellent yields. Significantly, this procedure features high functional group tolerance… read more here.
Keywords: cyclization aryl; nazarov cyclization; catalyst free; allenyl ketones ... See more keywords
Microwave-specific Enhancement of Nazarov Cyclization
Sign Up to like & getrecommendations! Published in 2021 at "Chemistry Letters"
DOI: 10.1246/cl.200617
Abstract: A copper-catalyzed Nazarov cyclization was carried out under conventional heating conditions and microwave conditions. Under strictly temperature-controlled conditions, the use of microwave irradia... read more here.
Keywords: cyclization; chemistry; nazarov cyclization; specific enhancement ... See more keywords
Optimization of Nazarov Cyclization of 2,4-Dimethyl-1,5-diphenylpenta-1,4-dien-3-one in Deep Eutectic Solvents by a Design of Experiments Approach
Sign Up to like & getrecommendations! Published in 2020 at "Molecules"
DOI: 10.3390/molecules25235726
Abstract: The unprecedented Nazarov cyclization of a model divinyl ketone using phosphonium-based Deep Eutectic Solvents as sustainable non-innocent reaction media is described. A two-level full factorial Design of Experiments was conducted for elucidating the effect of… read more here.
Keywords: dimethyl diphenylpenta; nazarov cyclization; deep eutectic; eutectic solvents ... See more keywords