Rare‐Earth‐Metal‐Catalyzed Kinetic Resolution of Chiral Aminoalkenes via Hydroamination: The Effect of the Silyl Substituent of the Binaphtholate Ligand on Resolution Efficiency
Sign Up to like & getrecommendations! Published in 2019 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.201900107
Abstract: The kinetic resolution of α‐substituted aminopentenes via intramolecular hydroamination was investigated using various 3,3′‐silyl‐substituted binaphtholate yttrium catalysts. High efficiencies in the kinetic resolution were observed for methyl‐, benzyl‐, and phenyl‐substituted substrates utilizing the cyclohexyldiphenylsilyl‐substituted catalyst… read more here.
Keywords: resolution; silyl; kinetic resolution; binaphtholate ... See more keywords
Silyl-protected propargyl glycine for multiple labeling of peptides by chemoselective silyl-deprotection
Sign Up to like & getrecommendations! Published in 2021 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2021.153093
Abstract: Abstract We synthesized Fmoc-propargyl glycine derivatives bearing different silyl protecting groups that can be readily introduced by using a standard solid-phase peptide coupling procedures. Taking advantage of the orthogonality between the different silyl protecting groups,… read more here.
Keywords: protected propargyl; silyl; propargyl glycine; silyl protected ... See more keywords
Synthesis of Silyl Aluminum Reagents: Relevance Toward Atomic Layer Deposition of Metal Silicides and the Serendipitous Synthesis of a Novel Al-Hydride Cluster.
Sign Up to like & getrecommendations! Published in 2020 at "Inorganic chemistry"
DOI: 10.1021/acs.inorgchem.0c02730
Abstract: The novel mono-silyl [(R3Si)AlX2]2, di-silyl [(R3Si)2AlX]2, tri-silyl (R3Si)3Al·Et2O, and -ate-complex [(R3Si)4Al]-·Li+(Et2O)2 have been synthesized by reaction of AlX3 (X = Cl, Br) with silyl lithium reagents (tBuMe2SiLi, Et3SiLi) in Et2O. Treatment of these compounds with… read more here.
Keywords: silyl aluminum; hydride cluster; silyl; synthesis ... See more keywords
Redox-Neutral Transformations of Carbon Dioxide Using Coordinatively Unsaturated Late Metal Silyl Amide Complexes.
Sign Up to like & getrecommendations! Published in 2022 at "Inorganic chemistry"
DOI: 10.1021/acs.inorgchem.2c03453
Abstract: Two-coordinate silylamido complexes of nickel and copper rapidly react with CO2 to selectively form a new cyanate ligand along with hexamethyldisiloxane byproducts. Mechanistic insight into these reactions was obtained from the synthesis of proposed intermediates,… read more here.
Keywords: carbon dioxide; dioxide using; neutral transformations; redox neutral ... See more keywords
Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.
Sign Up to like & getrecommendations! Published in 2019 at "Organometallics"
DOI: 10.1021/acs.organomet.9b00498
Abstract: We report the synthesis of unsaturated silacycles via an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form 5- and 6-membered silicon heterocycles. The effects of alkene substitution and tether… read more here.
Keywords: silyl heck; silyl; via intramolecular; synthesis unsaturated ... See more keywords
Tandem Insertion/[3,3]-Sigmatropic Rearrangement Involving the Formation of Silyl Ketene Acetals by Insertion of Rhodium Carbenes into S-Si Bonds.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c00229
Abstract: Allyl 2-diazo-2-phenylacetates are shown to react with trimethylsilyl thioethers in the presence of rhodium(II) catalysts to generate α-allyl-α-thio silyl esters. The transformation involves a tandem process involving formal rhodium-catalyzed insertion of the carbene group into… read more here.
Keywords: rhodium; silyl; insertion; silyl ketene ... See more keywords
Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans.
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DOI: 10.1021/acs.orglett.1c01838
Abstract: 4-Silyl-5,6-dihydropyrans undergo remarkably selective [1,4]-Wittig rearrangements to give silylcyclopropanes in good yields. The selectivity is independent of the silyl group, but it is influenced by the electronic character of the migrating center. Electron-rich and electron-neutral… read more here.
Keywords: silyl; selective wittig; wittig rearrangement; silyl dihydropyrans ... See more keywords
Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane: Synthesis of Enantioenriched α-Silyl Ketone.
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DOI: 10.1021/acs.orglett.7b02928
Abstract: A catalytic enantioselective Roskamp reaction of silyl diazoalkane to synthesize a highly optically active α-silyl ketone from aldehydes is described. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction provides α-chiral silyl ketones… read more here.
Keywords: reaction silyl; silyl; roskamp; roskamp reaction ... See more keywords
Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c04261
Abstract: Functionalized enantiopure organosilanes are important building blocks with applications in various fields of chemistry; nevertheless, asymmetric synthetic methods for their preparation are rare. Here we report the first organocatalytic enantioselective synthesis of tertiary silyl ethers… read more here.
Keywords: silyl ethers; synthesis stereogenic; organocatalytic asymmetric; asymmetric synthesis ... See more keywords
An Experimental Stereoselective Photochemical [1s,3s]-Sigmatropic Silyl Shift and the Existence of Silyl/Allyl Conical Intersections.
Sign Up to like & getrecommendations! Published in 2020 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.9b11579
Abstract: We report an experimental discovery and computational investigation of the first photochemical stereoselective [1,3]-sigmatropic silyl shift of an allylsilane. An organocatalytic enantioselective cascade annulation generates a trimethylsilyl-o-isotoluene reactant in >99:1 e.r., and this trimethylsilyl-o-isotoluene contains… read more here.
Keywords: silyl shift; silyl; sigmatropic silyl; silyl allyl ... See more keywords
Practical method for hydroxyl-group protection using strontium metal and readily available silyl chlorides.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc01105k
Abstract: We have found that the etherification of silyl-protected secondary alcohols proceeds smoothly in the presence of strontium metal using silyl chloride instead of the expensive, yet more reactive, and commonly used silyl triflate. The reaction… read more here.
Keywords: method hydroxyl; practical method; strontium metal; silyl ... See more keywords