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BINAP-CuH-catalysed enantioselective allylation using alkoxyallenes to access 1,2-,-diols.
Chem Sci
December 2024
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT) Hyderabad 500007 India https://cramhcu.wixsite.com/rambabu-chegondi.
Herein, we present an economical method for highly enantioselective and diastereoselective Cu-BINAP-catalysed reductive coupling of alkoxyallenes with a range of electronically and structurally diverse ketones to afford 1,2-,-diols, using PMHS as the hydride source. This reductive coupling has also been efficiently employed in the enantioselective desymmetrization of prochiral cyclic ketones harboring quaternary centres, in high yields with exclusive diastereoselectivity. Density Functional Theory (DFT) calculations are used to elucidate that the reaction is facilitated by a kinetically favourable "open" -enolate copper-alkoxyallene conformer, occurring at a lower Gibbs free energy barrier (by 3.
View Article and Find Full Text PDFChiral amido-oxazoline functionalized MCM-41: A sustainable heterogeneous catalyst for enantioselective Kharasch-Sosnovsky and Henry reactions.
Heliyon
November 2024
Laboratory of Asymmetric Synthesis, Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, 66177-15175, Iran.
In this study, a series of chiral amido-oxazoline ligands was synthesized with a primary focus on immobilizing the most effective ligands on MCM-41 mesoporous material. Following several attempts, the -nitro group of the chiral amido-oxazoline ligands was successfully reduced to amino group, enabling their immobilization on MCM-41. The resulting chiral heterogeneous amido-oxazoline ligands were characterized using various techniques, including FT-IR, XRD, TGA, SEM, TEM, EDX, and BET-BJH, confirming the successful immobilization of the amido-oxazoline ligands.
View Article and Find Full Text PDFEfforts toward the Total Synthesis of Thuggacin A.
Org Lett
November 2024
State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Thuggacin A () is a 17-membered-ring-polyketide antibiotic compound with excellent antituberculosis activity. The total synthesis of thuggacin A has not yet been reported so far. Herein, we disclose our efforts toward the convergent total synthesis of thuggacin A.
View Article and Find Full Text PDFSwitch of Five Contiguous Chiral Centers in the Synthesis of Both Enantiomers of Hajos-Parrish Ketone Analogs via Diphenylprolinol Silyl Ether-Mediated Domino Reaction.
Chemistry
January 2025
Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza-Aoba, Aoba-ku, Sendai, Miyagi, 980-8578, Japan.
Both enantiomers of functionalized Hajos-Parrish ketone (HPK) analogs were prepared with excellent diastereoselectivities and enantioselectivities using the same chiral catalyst under two slightly different conditions. In condition A, dioxane was used as the solvent with 3 equivalents of water. In condition B, acetonitrile was used as the solvent with 30 equivalents of water, followed by epimerization with a base in a one-pot.
View Article and Find Full Text PDFAccess to Alkenyl Cyclobutanols by Ni-Catalyzed Regio- and Enantio-Selective syn-Hydrometalative 4-exo-trig Cyclization of Alkynones.
Angew Chem Int Ed Engl
January 2025
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, and College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan, 430072, China.
Enantioselective synthesis of (spiro)cyclobutane derivatives poses significant challenges yet holds promising applications for both synthetic and medicinal chemistry. We report here a nickel-catalyzed asymmetric syn-hydrometalative 4-exo-trig cyclization of 1,4-alkynones to synthesize alkenyl cyclobutanols with a tetrasubstituted stereocenter. This strategy features a broad substrate scope, delivering a variety of trifluoromethyl-containing rigid (spiro)carbocycle skeletons in good yields with high enantioselectivities (up to 84 % yield and 98.
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