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Total syntheses of the parvistemoline alkaloids enabled by stereocontrolled Ir/Pd-catalyzed allylic alkylation.
Nat Commun
December 2024
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.
The functionalized polycycle with densely contiguous tertiary stereocenters is a formidable challenge in synthesizing the parvistemoline family of Stemona alkaloids. We herein report their catalytic, asymmetric total syntheses in 13-14 steps from commercially available 2-(methoxycarbonyl)-pyrrole, featuring the development and deployment of an Ir/Pd-synergistically-catalyzed allylation of α-non-substituted keto esters with secondary aryl-substituted alcohols, stereodivergently accessible to four stereoisomers. Using chiral Pd-enolate and Ir π-allyl complex under neutral conditions, no epimerization occurs.
View Article and Find Full Text PDFFacile access to chiral -1,2-diol derivatives Ir-catalyzed asymmetric hydrogenation of α-alkoxy-β-ketoesters.
Chem Commun (Camb)
December 2024
Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry and Medi-X Pingshan, Southern University of Science and Technology, Shenzhen 518055, People's Republic of China.
The iridium-catalyzed asymmetric hydrogenation of α-alkoxy-β-ketoesters dynamic kinetic resolution has been achieved with high efficiency and enantioselectivity. This strategy allows for the synthesis of differentiated -1,2-diol derivatives in high yields, exhibiting excellent enantio- and diastereoselectivity (up to 99% yield, 99% ee, and 99 : 1 dr). Additionally, high turnover number (TON) experiments (up to 1000 TON) and gram-scale synthesis of a key fragment of the potential drug Tesaglitazar were successfully performed, highlighting the protocol's potential for broader applications.
View Article and Find Full Text PDFHighly Enantioselective Synthesis of 3,3-Diarylpropyl Amines and 4-Aryl Tetrahydroquinolines via Ir-Catalyzed Asymmetric Hydrogenation.
Org Lett
December 2024
Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), Baldiri Reixac 10, 08028 Barcelona, Spain.
Article Synopsis
- Chiral nitrogen-containing compounds are essential in various industries, but their synthesis can be challenging due to a vast range of chemical possibilities.
- This research details a selective method to create 3,3-diarylallyl phthalimides, which, when treated with iridium catalysts, transform into 3,3-diarylpropyl amines with very high enantioselectivity (98-99% ee).
- The study highlights the role of alkene purity in achieving high enantioselectivity and illustrates how the resulting chiral propylamines can be used to make important bioactive drugs like tolterodine and tolpropamine.
Rational Design and Stereodivergent Construction of Enantioenriched Tetrahydro-β-Carbolines Containing Multistereogenic Centers.
J Am Chem Soc
October 2024
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Chiral tetrahydro-β-carbolines, as one of the most intriguing subtypes of indole alkaloids, have emerged as the privileged units in plenty of natural products and biologically active molecules with an impressive range of bioactive properties. However, the stereodivergent construction of these valuable skeletons containing multistereogenic centers from readily available starting materials remains very challenging, especially, in view of the introduction of an axial chirality. Herein, we developed an efficient method toward enantioenriched tetrahydro-β-carbolines with readily available tryptophan-derived aldimine esters and allylic carbonates under mild reaction conditions.
View Article and Find Full Text PDFDesign and Synthesis of Sulfur-Containing Tetradentate Ligands for Ir-Catalyzed Asymmetric Hydrogenation of Ketones.
Org Lett
October 2024
Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry and Medi-X Pingshan, Southern University of Science and Technology, Shenzhen 518055, People's Republic of China.
Developing highly active and enantioselective ligands for the asymmetric hydrogenation of ketones has consistently attracted significant attention from scientists. A series of novel tetradentate sulfur-containing ligands, termed as f-thiophamidol, were successfully designed and synthesized which exhibited excellent performance in the asymmetric hydrogenation of simple ketones (up to 99% yield, 99% ee) and α-substituted β-keto sulfonamides (up to 99% yield, 99% ee, 99:1 dr). The subsequent successful gram-scale experiments with high TON demonstrated the immense potential application value of this system in synthesizing drug molecules.
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