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Stereoselective Preparation and Pd-catalyzed Suzuki-Miyaura Cross-coupling of Alkenyl Sulfoximine.
Angew Chem Int Ed Engl
January 2025
Osaka University: Osaka Daigaku, Department of Applied Chemistry, JAPAN.
Although numerous transition-metal catalyzed cross-coupling reactions of alkenyl electrophiles with a sulfur(VI) leaving group, mainly alkenyl sulfones, have been developed, most rely heavily on highly nucleophilic Grignard reagents, and the use of organoboron reagents remains challenging. We report herein facile preparation and the following Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of alkenyl sulfoximine, a monoaza analog of sulfone. The condensation of alkyl sulfoximine with aldehydes, developed in this study, makes alkenyl sulfoximines more readily available.
View Article and Find Full Text PDFPhotoinduced Regiodivergent and Enantioselective Cross-Coupling of Glycine Derivatives with Hydrocarbon Feedstocks.
J Am Chem Soc
January 2025
Key Laboratory of Chemical Biology of Fujian Province, iChEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
Regiodivergent asymmetric synthesis represents a transformative strategy for the efficient generation of structurally diverse chiral products from a single set of starting materials, significantly enriching their enantiomeric composition. However, the design of radical-mediated regiodivergent and enantioselective reactions that can accommodate a wide range of functional groups and substrates has posed significant challenges. The obstacles primarily lie in switching the regioselectivity and achieving high enantiodiscrimination, especially when dealing with high-energy intermediates.
View Article and Find Full Text PDFHarnessing the Reactivity of Cyclopropenes in the Synthesis of Spiroketals via Putative Generation of Donor-Acceptor Cyclopropanes.
Org Lett
January 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Article Synopsis
- The study presents a method using TMSOTf to create spiroketal derivatives through hydroalkoxylation and cycloaddition reactions involving hydroxy cyclopropenes and aldehydes.
- This process generates a donor-acceptor cyclopropane intermediate, allowing for the efficient synthesis of [5.5]- and [6.5]-spiroketals.
- The resulting spirocyclic compounds can be further modified to produce complex polycyclic heterocycles through metal halogen exchange and copper-catalyzed reactions, with a decarboxylation step that introduces a fourth chiral center.
Studies on the Stereoselective Synthesis of Sacubitril via a Chiral Amine Transfer Approach.
Chem Asian J
December 2024
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.
We present a comprehensive account of our efforts directed towards the synthesis of sacubitril, a neprilysin inhibitor used in combination with valsartan and marketed as Entresto™. Our initial approach to the formal synthesis of sacubitril employed a chiral pool strategy, utilizing (S)-pyroglutamic acid as a key building block and Cu(I)-mediated Csp-Csp cross-coupling as a key transformation. Further investigations led to the development of chiral amine transfer (CAT) reagents-based stereoselective synthesis.
View Article and Find Full Text PDFFe-Catalyzed Structurally Divergent γ-Polyhaloalkylation of Siloxydienes.
Org Lett
December 2024
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, United States.
Regioselective γ-polyhaloalkylation is achieved using tetrahalomethanes or α,α,α-trihaloalkyl compounds and siloxydienes via Fe(II) catalysis. A range of siloxydienes are functionalized in good yields with high stereoselectivity under mild reaction conditions. Structural divergence is observed as either haloalkylated or haloalkenylated products are formed on the basis of the substitution pattern of the siloxydiene.
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