Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
JacsGold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals:Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. (Source: Organometallic Current)
Source: Organometallic Current - September 29, 2017 Category: Chemistry Tags: Gold Catalysis Source Type: blogs
Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane
JacsStereoselective Tandem Bis-Electrophile Couplings of Diborylmethane: A copper-catalyzed three-component linchpin coupling method for the stereoselective union of readily available epoxides and allyl electrophiles is disclosed. Transformations employ [B(pin)]2-methane as a conjunctive reagent, resulting in the formation of two C –C bonds at a single carbon center bearing a C(sp3) organoboron functional group. (Source: Organometallic Current)
Source: Organometallic Current - September 28, 2017 Category: Chemistry Tags: Borylation Cu catalyzed Source Type: blogs
Intermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines
We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case ofanti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. (Source: Organometallic Current)
Source: Organometallic Current - September 28, 2017 Category: Chemistry Tags: Hydroamination Rh Catalyzed Source Type: blogs
Transition Metal Free C –N Bond Forming Dearomatizations and Aryl C–H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent
AngewchemTransition Metal Free C –N Bond Forming Dearomatizations and Aryl C–H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent: We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C –N bond forming dearomatization or aryl C–H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines. (Source: Organometallic Current)
Source: Organometallic Current - September 28, 2017 Category: Chemistry Tags: Dearomatization Metal free Source Type: blogs
Direct β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis
JacsDirect β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis: The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes. (Source: Organometallic Current)
Source: Organometallic Current - September 28, 2017 Category: Chemistry Tags: Continuous Flow Synthesis Hydrocarboxylation Photoredox Catalysis Source Type: blogs
Bioinspired Total Synthesis of ( −)‐Vescalin: A Nonahydroxytriphenoylated C‐Glucosidic Ellagitannin
AngewchemBioinspired Total Synthesis of ( −)‐Vescalin: A Nonahydroxytriphenoylated C‐Glucosidic Ellagitannin: The first total synthesis of the 2,3,5 ‐O‐(S,R)‐nonahydroxytriphenoylated (NHTP) C‐glucosidic ellagitannin (−)‐vescalin was accomplished through a series of transformations mimicking the sequence of events... (Source: Organometallic Current)
Source: Organometallic Current - September 28, 2017 Category: Chemistry Tags: Total synthesis Source Type: blogs
Organocatalytic Intramolecular [4 2] Cycloaddition Between In Situ Generated Vinylidene ortho ‐Quinone Methides and Benzofurans
AngewchemOrganocatalytic Intramolecular [4 2] Cycloaddition Between In Situ Generated Vinylidene ortho ‐Quinone Methides and Benzofurans: Described herein is the enantioselective construction of oxygen ‐containing [5‐6‐5] tricyclic heterocycles by an organocatalyzed asymmetric [4+2] cycloaddition of vinylidene ortho‐quinone methides and benzofurans.... (Source: Organometallic Current)
Source: Organometallic Current - September 28, 2017 Category: Chemistry Tags: Cycloaddition organocatalysis Source Type: blogs
Enantioselective Total Synthesis of ( −)‐Deoxoapodine
AngewchemEnantioselective Total Synthesis of ( −)‐Deoxoapodine: The first enantioselective total synthesis of ( −)‐deoxoapodine is described. Our synthesis of this hexacyclic aspidosperma alkaloid includes an efficient molybdenum‐catalyzed enantioselective ring‐closing... (Source: Organometallic Current)
Source: Organometallic Current - September 28, 2017 Category: Chemistry Tags: Biomimetic Synthesis Total synthesis Source Type: blogs
Catalytic Asymmetric [4 2]-Cycloaddition of Dienes with Aldehydes
JacsCatalytic Asymmetric [4 2]-Cycloaddition of Dienes with Aldehydes: Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Br ønsted acid catalysts of the hetero-Diels–Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically...
Source: Organometallic Current - September 27, 2017 Category: Chemistry Tags: Cycloaddition Hetero-Diels-Alders-Reactions Source Type: blogs
Synthesis of Benzosiloles by Intramolecular anti-Hydroarylation via ortho-C –H Activation of Aryloxyethynyl Silanes
JacsSynthesis of Benzosiloles by Intramolecular anti-Hydroarylation via ortho-C –H Activation of Aryloxyethynyl Silanes:Straightforward synthesis of benzosiloles was achieved by the invention of Pd/acid-catalyzed intramolecularanti-hydroarylation of aryloxyethynyl(aryl)silanes viaortho-C –H bond activation. The aryloxy group bound to the ethynyl carbon is the key factor for this transformation. (Source: Organometallic Current)
Source: Organometallic Current - September 27, 2017 Category: Chemistry Tags: C-H Activation Pd Catalyzed Source Type: blogs
Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible ‐Light Photoredox Catalysis
AngewchemEfficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible ‐Light Photoredox Catalysis: We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro ‐Smiles rearrangement by visible‐light photoredox catalysis at ambient temperature. Transition... (Source: Organometallic Current)
Source: Organometallic Current - September 27, 2017 Category: Chemistry Tags: Photoredox Catalysis Visible light Source Type: blogs
One ‐Step Multigram‐Scale Biomimetic Synthesis of Psiguadial B
AngewchemOne ‐Step Multigram‐Scale Biomimetic Synthesis of Psiguadial B: A gram ‐scale synthesis of psiguadial B, a purported inhibitor of human hepatoma cell growth, has been achieved in one step by a biomimetic three‐component coupling of caryophyllene, benzaldehyde, and diformylphloroglucinol.... (Source: Organometallic Current)
Source: Organometallic Current - September 27, 2017 Category: Chemistry Tags: Natural products Total synthesis Source Type: blogs
Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones
AngewchemHydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones: An efficient and simple radical chain reaction to convert terminal alkynes into arenesulfonylmethylcyclopentanes is described. The reaction involves a radical addition –translocation–cyclization process... (Source: Organometallic Current)
Source: Organometallic Current - September 27, 2017 Category: Chemistry Tags: Radical Reactions Sulfonation Source Type: blogs
α‐Carbonyl Cations in Sulfoxide‐Driven Oxidative Cyclizations
Angewchemα‐Carbonyl Cations in Sulfoxide‐Driven Oxidative Cyclizations: The selective, metal ‐free generation of α‐carbonyl cations from simple internal alkynes was accomplished by the addition of a sulfoxide to a densely substituted vinyl cation. The high reactivity of the... (Source: Organometallic Current)
Source: Organometallic Current - September 25, 2017 Category: Chemistry Tags: Oxidative Coupling Source Type: blogs
Pd ‐PEPPSI‐IPent‐SiO2: A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow
AngewchemPd ‐PEPPSI‐IPent‐SiO2: A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow: A silica ‐supported precatalyst, Pd‐PEPPSI‐IPent‐SiO2, has been prepared and evaluated for its proficiency in the Negishi cross‐coupling of hindered and electronically deactivated coupling partners. The... (Source: Organometallic Current)
Source: Organometallic Current - September 25, 2017 Category: Chemistry Tags: Continuous Flow Synthesis Negishi coupling Pd Catalyzed Source Type: blogs
