Palladium-Catalyzed Carbene Migratory Insertion/Carbonylation Cascade Reaction: Synthesis of 2-Indolones with a C3 All-Carbon Quaternary Center.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00073
Abstract: An attractive palladium-catalyzed three-component reaction of ortho-amino aryl diazo esters, allyl carboxylates, and carbon monoxide (CO) has been developed. This catalytic system rendered domino carbene migratory insertion and carbonylation. Remarkably, 2-indolones 3 with a C3… read more here.
Keywords: migratory insertion; palladium catalyzed; carbon quaternary; insertion carbonylation ... See more keywords
Rhodium-Catalyzed Desymmetric Arylation of γ,γ-Disubsituted Cyclohexadienones: Asymmetric Synthesis of Chiral All-Carbon Quaternary Centers.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00225
Abstract: The desymmetric arylation of prochiral cyclohexadienones with ArZnCl in the presence of an (R)-segphos-rhodium catalyst gave high yields of the corresponding cyclohexenones, which contain a chiral arylated carbon center at the β-position and a chiral… read more here.
Keywords: carbon; chiral carbon; carbon quaternary; rhodium catalyzed ... See more keywords
Catalytic Asymmetric Decarboxylative Michael Addition To Construct an All-Carbon Quaternary Center with 3-Alkenyl-oxindoles.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00411
Abstract: The first highly enantioselective asymmetric decarboxylative addition of β-keto acids with 3-alkenyl-oxindoles bearing an all-carbon quaternary stereocenter have been developed. The relevant products were acquired in 49-98% yields with 88-98% enantioselectivities in the presence of… read more here.
Keywords: addition; carbon quaternary; asymmetric decarboxylative; alkenyl oxindoles ... See more keywords
Dearomatizing Cyclization of 2-Iodoindoles by Oxidative NHC Catalysis to Access Spirocyclic Indolenines and Oxindoles Bearing an All Carbon Quaternary Stereocenter.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01851
Abstract: An intramolecular dearomatizing spirocyclization of indoles by oxidative N-heterocyclic carbene catalysis is reported. C2-iodinated indoles are used as substrates in combination with aroyl azolium ions as acceptors, which provides C2-iodinated indolenines containing an all carbon… read more here.
Keywords: catalysis; carbon quaternary; access; quaternary stereocenter ... See more keywords
Enantioselective Formation of All-Carbon Quaternary Stereocenters in gem-Difluorinated Cyclopropanes via Rhodium-Catalyzed Stereoablative Kinetic Resolution.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02410
Abstract: Herein, we report an effective method to offer chiral gem-difluorinated cyclopropanes containing an all-carbon quaternary stereocenter by rhodium-catalyzed stereoablative kinetic resolution. The activation of a sterically hindered all-carbon quaternary C-C bond through oxidative addition with… read more here.
Keywords: rhodium catalyzed; gem difluorinated; difluorinated cyclopropanes; carbon quaternary ... See more keywords
Selective Construction of All-Carbon Quaternary Centers via Relay Catalysis of Indole C-H Functionalization/Allylic Alkylation.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03543
Abstract: Herein, a novel [Rh]2-catalyzed three-component reaction of readily accessible indoles, diazo compounds, and allylic compounds is developed via a relay carbene-induced C-H functionalization and allylic alkylation process, affording diverse C3-substituted indoles bearing all-carbon quaternary centers… read more here.
Keywords: carbon; functionalization allylic; carbon quaternary; via relay ... See more keywords
Pd-Catalyzed Cascade Intramolecular Heck Cyclization/Dearomatization of Indoles for the Construction of Two All-Carbon Quaternary Centers.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03691
Abstract: A facile Pd-catalyzed cascade of intramolecular Heck cyclization/alkylpalladium activated dearomatization of aryl alkyne-tethered indole is described. In this single step two nonadjacent all-carbon quaternary centers, two nitrogen-containing heterocycles, and three C(sp2)-C(sp3) bonds are efficiently furnished.… read more here.
Keywords: intramolecular heck; catalyzed cascade; cascade intramolecular; carbon quaternary ... See more keywords
Catalytic Enantioselective Synthesis of 2,3'-Bis(indolyl)methanes Bearing All-Carbon Quaternary Stereocenters via 2-Indole Imine Methides.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.2c04109
Abstract: An organocatalytic enantioselective formal hydroarylation of 2-vinyl indoles for the preparation of enantioenriched 2,3'-bis(indolyl)methanes bearing an all-carbon quaternary stereocenter is described. This reaction features mild conditions, low catalyst loading, excellent efficiency and enantioselectivity. The obtained… read more here.
Keywords: bearing carbon; indolyl methanes; carbon quaternary; bis indolyl ... See more keywords
Regio- and Stereoselective Alkenylation of Allenoates with gem-Difluoroalkenes: Facile Access to Fluorinated 1,4-Enynes Bearing an All-Carbon Quaternary Center.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b00775
Abstract: A regio- and stereoselective synthesis of fluorinated 1,4-enynes bearing an all-carbon quaternary center at the propargylic position is developed. The synthesis starts from readily available allenoates and gem-difluoroalkenes and proceeds via a key alkynylenolate intermediate… read more here.
Keywords: enynes bearing; carbon quaternary; fluorinated enynes; regio stereoselective ... See more keywords
Boryl Radicals Enabled a Three-Step Sequence to Assemble All-Carbon Quaternary Centers from Activated Trichloromethyl Groups.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c05798
Abstract: The construction of diversely substituted all-carbon quaternary centers has been a longstanding challenge in organic synthesis. Methods that add three alkyl substituents to a simple C(sp3) atom rely heavily on lengthy multiple processes, which usually… read more here.
Keywords: step; carbon; carbon quaternary; trichloromethyl groups ... See more keywords
Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine.
Sign Up to like & getrecommendations! Published in 2018 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.8b05386
Abstract: A novel chiral spirocyclic amide (SPA)-derived triazolium organocatalyst has been designed and demonstrated to effect asymmetric homo- and heterodialkylations of various bisoxindoles, enabling enantioselective construction of vicinal all-carbon quaternary stereocenters. These reactions feature excellent enantio-… read more here.
Keywords: carbon quaternary; quaternary stereocenters; vicinal carbon; total synthesis ... See more keywords