Copper(I)-Catalyzed Synthesis of Unsymmetrical All-Carbon Bis-Quaternary Centers at the Opposing α-Carbons of Cyclohexanones
Sign Up to like & getrecommendations! Published in 2022 at "Organic Letters"
DOI: 10.1021/acs.orglett.2c01890
Abstract: We describe a new synthetic reaction that generates all-carbon bis-quaternary centers at the opposing side of α-carbons in cyclohexanone with four different substituents in a controlled manner. Catalyzed by Cu(MeCN)4BF4 salt, this chemistry is proposed… read more here.
Keywords: carbon bis; centers opposing; bis quaternary; copper catalyzed ... 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
Access to All-Carbon Quaternary Centers by Photocatalytic Fluoroalkylation of α-Halo Carbonyl Compounds.
Sign Up to like & getrecommendations! Published in 2024 at "Organic letters"
DOI: 10.1021/acs.orglett.4c00041
Abstract: Perfluoroalkyl groups have become significantly important in pharmaceutical and agrochemical applications. In this study, we present a visible light-mediated photoredox neutral strategy for the fluoroalkylation of tertiary alkyl chlorides under transition-metal-free conditions. This method allows… read more here.
Keywords: carbon quaternary; access carbon; centers photocatalytic; quaternary centers ... See more keywords
Cascade Grignard Addition: Propargyl Claisen Rearrangement for the Stereoselective Synthesis of α‑Allene Quaternary Centers in Cyclohexanones
Sign Up to like & getrecommendations! Published in 2025 at "Organic Letters"
DOI: 10.1021/acs.orglett.5c02006
Abstract: We report a new method for the enantio- and diastereoselective synthesis of α-allene quaternary centers in fully substituted cyclohexanones at the α-positions. This reaction involves asymmetric 1,2-carbonyl addition to 2-O-propargyl enones using a mixture of… read more here.
Keywords: addition propargyl; synthesis allene; allene quaternary; propargyl claisen ... See more keywords
Enantioselective Synthesis of 1,2-Diamines Containing Tertiary and Quaternary Centers through Rhodium-Catalyzed DYKAT of Racemic Allylic Trichloroacetimidates.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.7b02256
Abstract: The amination of racemic secondary and tertiary allylic trichloroacetimidates possessing β-nitrogen substituents and proximal nitrogen-containing heterocycles, via chiral diene-ligated rhodium-catalyzed dynamic kinetic asymmetric transformations (DYKAT), provides branched allylic 1,2-diamines with high enantioselectivity. The catalytic system… read more here.
Keywords: allylic trichloroacetimidates; rhodium catalyzed; tertiary quaternary; synthesis diamines ... See more keywords
Palladium-Catalyzed Chemoselective Activation of sp3 vs sp2 C-H Bonds: Oxidative Coupling To Form Quaternary Centers.
Sign Up to like & getrecommendations! Published in 2019 at "ACS catalysis"
DOI: 10.1021/acscatal.9b00091
Abstract: The oxidative activation of alkyl C-H bonds vs arene C-H bonds with Pd(OAc)2 has been found to be generalizable to a number of nucleophilic substrates allowing the formation of a range of hindered quaternary centers.… read more here.
Keywords: activation; catalyzed chemoselective; chemoselective activation; activation sp3 ... 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
Diversification reactions of γ-silyl allenyl esters: selective conversion to all-carbon quaternary centers and γ-allene dicarbinols.
Sign Up to like & getrecommendations! Published in 2017 at "Chemical communications"
DOI: 10.1039/c7cc01708a
Abstract: The unique reactivity of γ-silyl allenyl esters is described. Taking advantage of the silyl group as a fluoride acceptor, these allenoates readily underwent addition to a variety of electrophiles to selectively yield products with all-carbon… read more here.
Keywords: silyl allenyl; allenyl esters; carbon quaternary; reactions silyl ... See more keywords
Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers
Sign Up to like & getrecommendations! Published in 2025 at "Beilstein Journal of Organic Chemistry"
DOI: 10.3762/bjoc.21.63
Abstract: This study introduces a highly selective hydrocyanation method based on copper-catalyzed hydroalumination of allenes with diisobutylaluminum hydride, followed by the regio- and stereoselective allylation with p-toluenesulfonyl cyanide. The proposed methodology is efficient for accessing acyclic… read more here.
Keywords: carbon quaternary; hydrocyanation; unsaturated nitriles; nitriles carbon ... See more keywords