Phosphine‐Catalyzed Synthesis and Cytotoxic Evaluation of Michael Adducts of the Sesquiterpene Lactone Arglabin
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DOI: 10.1002/cmdc.202400045
Abstract: A general method for chemo‐ and diastereoselective modification of anticancer natural product arglabin with nitrogen‐ and carbon‐centered pronucleophiles under the influence of nucleophilic phosphine catalysts was developed. The locked s‐cis‐geometry of α‐methylene‐γ‐butyrolactone moiety of arglabin… read more here.
Keywords: cell lines; sesquiterpene lactone; arglabin; phosphine catalyzed ... See more keywords
Phosphine‐Catalyzed 1,6‐Addition and Tandem Addition/Self‐Aldol Condensation Reactions of para‐Quinone Methides with Thiols
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DOI: 10.1002/ejoc.202400130
Abstract: Phosphine‐catalyzed chemodivergent reactions of para‐quinone methides (p‐QMs) affording a wide variety of diarylmethyl thioether derivatives have been reported. In the transformation presented in this work, P(4‐FC6H4)3 catalyzed the direct 1,6‐addition of p‐QMs with thiols, whereas… read more here.
Keywords: para quinone; quinone methides; addition; tandem addition ... See more keywords
Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates.
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DOI: 10.1021/acs.orglett.1c01214
Abstract: A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael… read more here.
Keywords: phosphine catalyzed; coupling benzyl; halides fumarates; cross coupling ... See more keywords
Phosphine-Catalyzed Internal Redox [4 + 2] Annulation between 1,4-Enynoates and Electron-Deficient Alkenes.
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DOI: 10.1021/acs.orglett.1c03206
Abstract: Herein we describe a phosphine-catalyzed internal redox [4 + 2] annulation of 1,4-enynoates with electron-deficient alkenes, in which the γ- and φ-C(sp3)-H of the enynoates are formally oxidized for the annulation while the alkynyl moiety… read more here.
Keywords: phosphine catalyzed; annulation; annulation enynoates; internal redox ... See more keywords
Phosphine-Catalyzed Intramolecular Vinylogous Aldol Reaction of α-Substituted Enones.
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DOI: 10.1021/acs.orglett.1c03913
Abstract: We demonstrate the first phosphine-catalyzed intramolecular vinylogous aldol reaction (IVAR) of α-substituted enones. This strategy provides access to various pentannulated (hetero)arenes and dibenzocycloheptanones incorporated with two contiguous stereocenters, one of which is an all-carbon quaternary… read more here.
Keywords: phosphine catalyzed; intramolecular vinylogous; vinylogous aldol; aldol reaction ... See more keywords
Phosphine-Catalyzed Dearomative [3 + 2] Cycloaddition of Benzoxazoles with a Cyclopropenone
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DOI: 10.1021/acs.orglett.1c04045
Abstract: The triphenylphosphine-catalyzed dearomative [3 + 2] cycloaddition of benzoxazoles with 1,2-diphenylcyclopropenone is herein described. The reaction scope, mechanism, and possible future applications of this rare organocatalyzed cycloaddition are herein discussed. read more here.
Keywords: cycloaddition benzoxazoles; catalyzed dearomative; benzoxazoles cyclopropenone; dearomative cycloaddition ... See more keywords
Enantioselective Synthesis of Pyrrolidines by a Phosphine-Catalyzed γ-Umpolung/β-Umpolung Cascade.
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DOI: 10.1021/acs.orglett.2c00785
Abstract: Herein, we report an enantioselective catalytic annulation of electron-poor allenes with aminocrotonates. The reaction proceeds by the umpolung γ-amination of the allenoate and β-umpolung intramolecular conjugate addition. The reaction provides ready access to pyrrolidines using… read more here.
Keywords: umpolung umpolung; enantioselective synthesis; synthesis pyrrolidines; pyrrolidines phosphine ... See more keywords
Phosphine-Catalyzed Sequential [3 + 2]/[3 + 2] Annulation between Allenoates and Arylidenemalononitriles for the Enantioselective Construction of Bicyclo[3,3,0]octenes and Cyclopenta[c]quinolinones.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01352
Abstract: A highly diastereo- and enantioselective phosphine-catalyzed sequential [3 + 2]/[3 + 2] annulation of allenoates with arylidenemalononitriles has been developed. This reaction allows for the facile construction of multifunctionalized cis-fused bicyclic[3,3,0]octene scaffolds, encompassing three consecutive… read more here.
Keywords: phosphine catalyzed; catalyzed sequential; sequential annulation; annulation allenoates ... See more keywords
Phosphine-Catalyzed (4 + 2) Annulation of Allenoates with Benzofuran-Derived Azadienes and Subsequent Thio-Michael Addition.
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DOI: 10.1021/acs.orglett.2c01500
Abstract: A phosphine-catalyzed (4 + 2) annulation of tetrahydrobenzofuranone-derived allenoates and benzofuran-derived azadienes (BDAs) has been achieved to construct the decahydro-2H-naphtho[1,8-bc]furan derivatives, which were subsequently treated with 4-methylbenzenethiol and trimethylamine to produce thio-Michael addition products in… read more here.
Keywords: derived azadienes; catalyzed annulation; allenoates benzofuran; thio michael ... See more keywords
C-C Bond Activation of Cyclopropanes Enabled by Phosphine-Catalyzed In Situ Formation of High-Strain Methylenecycopropane Intermediate.
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DOI: 10.1021/acs.orglett.2c02201
Abstract: An effective strategy for the ring-opening/elaboration of cyclopropanes by phosphine catalyst is documented, providing the 2,4-pentadiene sulfonamides and isoindolines in moderate to good yields. The key to the success of this reaction is phosphine-catalyzed introduction… read more here.
Keywords: activation cyclopropanes; cyclopropanes enabled; bond activation; enabled phosphine ... See more keywords
Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of N-Arylmaleimides.
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DOI: 10.1021/acs.orglett.2c02208
Abstract: Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This desymmetrization process allows for quick… read more here.
Keywords: phosphine catalyzed; cycloaddition desymmetrization; atroposelective formal; formal cycloaddition ... See more keywords