Diphenylprolinol silyl ether was found to catalyze the formal carbo [3 + 3] cycloaddition reaction through the domino reaction via the Michael reaction, followed by Knoevenagel condensation of the alpha,beta-unsaturated aldehyde and dimethyl 3-oxopentanedioate, affording substituted cyclohexenone derivatives with excellent enantioselectivity.
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Switch of Five Contiguous Chiral Centers in the Synthesis of Both Enantiomers of Hajos-Parrish Ketone Analogs via Diphenylprolinol Silyl Ether-Mediated Domino Reaction.
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November 2024
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.
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J Org Chem
August 2024
Department of Chemistry, Indian Institute of Technology Gandhinagar, Palaj, Gandhinagar, Gujarat 382055, India.
A general methodology for the asymmetric synthesis of α-arylcyclohexeneones from arylacetones and α,β-unsaturated aldehydes catalyzed by diphenylprolinol silyl ether followed by -TSA-mediated cyclization is developed. A variety of arylacetones and α,β-unsaturated aldehydes were successfully converted to α-arylcyclohexeneones in 34-67% yield, 10:1-100:0 , and 81-99% . The scalability of this methodology by a gram-scale synthesis and their utility by converting the product to the corresponding epoxide, alcohol, and diol are demonstrated.
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Department of Chemistry, Graduate School of Science, Tohoku University Sendai 980-8578 Japan
Highly substituted -hydrindanes were synthesized by the three-component coupling reactions of 1,3-diethyl 2-(2-oxopropylidene)propanedioate and two different α,β-unsaturated aldehydes catalyzed by diphenylprolinol silyl ether. The reaction proceeds two successive independent catalytic domino reactions in a one-pot reaction by a single chiral catalyst. Domino reactions involve Michael/Michael and Michael/aldol reactions to afford -hydrindanes with excellent diastereoselectivity and nearly optically pure form.
View Article and Find Full Text PDFOrganocatalytic Asymmetric Vinylogous Michael Addition of Electron-Deficient Aryl Alkane Nucleophiles to Enals.
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College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, China.
We report herein a protocol for an organocatalyzed asymmetric vinylogous Michael addition of aryl alkane nucleophiles with enals under base- and additive-free conditions. A series of allylic building blocks were obtained in 60%-93% yield and 88-99% ee with 20 mol % diphenylprolinol silyl ether as catalyst. This protocol has advantages such as excellent chemoselectivity and regioselectivity, good tolerance of functionalities, and simple reaction conditions.
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July 2023
Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
Substituted quinolines, tricyclic and tetracyclic molecules with a quinoline moiety are synthesized by a domino reaction from dicyanoalkenes and 3-aryl-pent-2-en-4-ynals in one pot. We established two methods: one is catalyzed by chiral diphenylprolinol silyl ether, and the other is catalyzed by di(2-ethyl)hexylamine, in combination with p-nitrophenol. A wide variety of dicyanoalkenes can be employed.
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