- Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives
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A method for amide-directed Ni-catalyzed diastereoselective arylboration of cyclopentenes is disclosed. The reaction allows for the synthesis of sterically congested cyclopentane scaffolds that contain an easily derivatized boronic ester and amide functional handles. The nature of the amide directing group and its influence on the reaction outcome are investigated and ultimately reflect a predictably selective reaction based on the solvent and base counterion.
- Lambright, Alison L.,Liu, Yanyao,Joyner, Isaac A.,Logan, Kaitlyn M.,Brown, M. Kevin
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supporting information
p. 612 - 616
(2021/01/26)
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- THIADIAZINE DERIVATIVES
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The invention relates to thiadiazine derivatives, or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof, as well as to pharmaceutical compositions containing
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Page/Page column 43
(2020/02/06)
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- Zn-ProPhenol Catalyzed Enantioselective Mannich Reaction of 2 H-Azirines with Alkynyl Ketones
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The enantioselective Mannich reaction of 2H-azirines with alkynyl ketones is achieved under Zn-ProPhenol catalysis, delivering various aziridines with vicinal tetrasubstituted stereocenters in high yields with excellent enantioselectivities. The bimetalli
- Trost, Barry M.,Zhu, Chuanle
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supporting information
p. 9683 - 9687
(2020/12/21)
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- Copper-Catalyzed Enantioselective Arylative Desymmetrization of Prochiral Cyclopentenes with Diaryliodonium Salts
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A copper-catalyzed enantioselective arylative desymmetrization of prochiral cyclopentenes with diaryliodonium salts was developed. In the presence of a catalytic amount of a chiral copper–bisoxazoline complex, which was generated in situ, the reaction of 4-substituted or 4,4-disubstituted cyclopent-1-enes with diaryliodonium hexafluoroarsenates afforded the chiral arylated products in good yields with excellent enantioselectivity. A cyclohexyl-containing Box ligand was essential for the high enantioselectivity. Transformation of the enantiomerically enriched adducts into other chiral building blocks is also documented.
- Wu, Hua,Wang, Qian,Zhu, Jieping
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supporting information
p. 2721 - 2725
(2018/02/09)
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- Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions: Synthetic and Mechanistic Insights
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Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 °C. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.
- Coe, Jotham W.,Bianco, Krista E.,Boscoe, Brian P.,Brooks, Paige R.,Cox, Eric D.,Vetelino, Michael G.
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p. 9964 - 9970
(2007/10/03)
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