91266-03-4Relevant articles and documents
Survey of synthetic approaches to natural (peyssonenynes) and unnatural acetoxyenediynes
Garcia-Dominguez, Patricia,Alvarez, Rosana,De Lera, Angel R.
, p. 4762 - 4782 (2012)
Four convergent synthetic approaches to acetoxyenediynes have been explored to gain access to peyssonenynes A and B, which are natural products isolated from the red alga Peyssonelia caulifera. After optimization of the routes with a palmitic acid based m
Alkyne Aminopalladation/Heck and Suzuki Cascades: An Approach to Tetrasubstituted Enamines
Geffers, Finn J.,Jones, Peter G.,Kurth, Florens R.,Werz, Daniel B.
supporting information, p. 14846 - 14850 (2021/10/19)
Alkyne aminopalladation reactions starting from tosylamides are reported. The emerging vinylic Pd species are converted either in an intramolecular Heck reaction with olefinic units or in an intermolecular Suzuki reaction by using boronic acids exhibiting broad functional group tolerance. Tetra(hetero)substituted tosylated enamines are obtained in a simple one-pot process.
Enantioselective Catalytic Crotylboration Based Syntheses of the C(7)–C(18(20)) Fragments of Polyketides Isolated from Streptomyces gramineus
Morávková, Terézia,Bedná?ová, Eva,Kotora, Martin
, (2021/10/20)
A general modular enantioselective synthetic approach to the C(7)–C(18) and the C(7)–C(20) fragment belonging to E-492, actinofuranone A, and JBIR-108 was developed. The crucial synthetic step relies on highly enantioselective crotylboration of aldehydes
Migratory Hydrogenation of Terminal Alkynes by Base/Cobalt Relay Catalysis
Liu, Bingxue,Liu, Qiang,Liu, Xufang
supporting information, p. 6750 - 6755 (2020/03/13)
Migratory functionalization of alkenes has emerged as a powerful strategy to achieve functionalization at a distal position to the original reactive site on a hydrocarbon chain. However, an analogous protocol for alkyne substrates is yet to be developed. Herein, a base and cobalt relay catalytic process for the selective synthesis of (Z)-2-alkenes and conjugated E alkenes by migratory hydrogenation of terminal alkynes is disclosed. Mechanistic studies support a relay catalytic process involving a sequential base-catalyzed isomerization of terminal alkynes and cobalt-catalyzed hydrogenation of either 2-alkynes or conjugated diene intermediates. Notably, this practical non-noble metal catalytic system enables efficient control of the chemo-, regio-, and stereoselectivity of this transformation.
A bio-inspired cascade and a late-stage directed sp3 C–H lithiation enables a concise total synthesis of (?)-virosaine A
Hughes, Jonathan M.E.,Gleason, James L.
supporting information, p. 759 - 768 (2018/01/01)
The asymmetric total synthesis of (?)-virosaine A was achieved in 9% overall yield from commercially/readily available starting materials. Inspired by an intriguing biosynthetic proposal, a novel cascade reaction sequence was developed to efficiently cons
N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE
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Paragraph 0409, (2018/03/28)
The invention relates to compounds of formula (I), or a salt thereof wherein R1, A, L, and R2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are ανβ1 integrin inhibitors that are useful for treating tissue specific fibrosis.
Gold(III)-Catalyzed Regioselective Oxidation/Cycloisomerization of Diynes: An Approach to Fused Furan Derivatives
Li, Jian,Xing, Hong-Wen,Yang, Fang,Chen, Zi-Sheng,Ji, Kegong
supporting information, p. 4622 - 4626 (2018/08/07)
The first gold(III)-catalyzed regioselective oxidation/cycloisomerization of diynes 1 with pyridine N-oxide as the oxidant was developed, providing a range of synthetically valuable and useful fused furan derivatives 3 in moderate to good yields. Control experiments and the confirmation structure of minor products 5 suggest that this chemistry was a concerted gold(III)-catalyzed oxidation/SN2′-type addition/cyclization process via a β-gold vinyloxypyridinium intermediate and a putative vinyl cation intermediate.
Rhodium-catalyzed endo -selective epoxide-opening cascades: formal synthesis of (-)-brevisin
Armbrust, Kurt W.,Beaver, Matthew G.,Jamison, Timothy F.
supporting information, p. 6941 - 6946 (2015/06/16)
[Rh(CO)2Cl]2 is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Synth
A Remarkably Simple Hybrid Surfactant-NHC Ligand, Its Gold-Complex, and Application in Micellar Catalysis
Rühling, Andreas,Galla, Hans-Joachim,Glorius, Frank
supporting information, p. 12291 - 12294 (2015/08/25)
A combination of an N-heterocyclic carbene (NHC) ligand and a structurally simple surfactant has been realized, the hybrid surfactant-NHC. The related gold complex was synthesized, fully characterized, and applied in catalysis. This remarkably simple strategy allows, in combination with a co-surfactant, the application of gold catalysis in water. Just merge it! The hybrid of a surfactant and an N-heterocyclic carbene (NHC) ligand is reported and applied for the synthesis of the derived gold complex (see scheme). The new resulting NHC-based metallosurfactant can interact with surfactants to form micelles and allows micellar catalysis for gold catalysis in water.
Pd(0)-catalyzed alkene oxy- and aminoalkynylation with aliphatic bromoacetylenes
Nicolai, Stefano,Sedigh-Zadeh, Raha,Waser, Jeroime
, p. 3783 - 3801 (2013/06/26)
Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins constitute one of the most efficient methods to access them. In this context, oxy- and aminoalkynylation are especially important reactions, because of the numerous transformations possible with the triple bond of acetylenes, yet these methods have been limited to the use of silyl protected acetylenes. Herein, we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes, which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally, a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.
