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.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
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
Phosphine-Catalyzed Tandem Annulation of Allenylic Alcohols with 1,1-Dicyanoalkenes.
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DOI: 10.1021/acs.orglett.3c01066
Abstract: The phosphine-catalyzed tandem annulation of allenylic alcohols with 1,1-dicyanoalkenes has been developed, giving various bicyclic tetrahydrocyclopentafuran derivatives in 40-89% yields with moderate to excellent diastereoselectivities. The fused ring was furnished through a sequential (3 +… read more here.
Keywords: catalyzed tandem; annulation; allenylic alcohols; phosphine catalyzed ... See more keywords
Phosphine-Catalyzed Domino β/γ-Additions of Benzofuranones with Allenoates: A Method for Unsymmetrical 3,3-Disubstituted Benzofuranones.
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DOI: 10.1021/acs.orglett.7b01482
Abstract: A phosphine-catalyzed domino process of benzofuranones with allenoates has been developed which furnishes highly functionalized unsymmetrical 3,3-disubstituted benzofuranones in synthetically useful yields. The mechanism for the transformation is a tandem β-umpolung/γ-umpolung process. read more here.
Keywords: phosphine catalyzed; unsymmetrical disubstituted; catalyzed domino; disubstituted benzofuranones ... See more keywords