A new method for seven-membered ring annulation has been devised by an intramolecular cross-coupling of cyclopropanols and aryl/alkenyl halides. This cyclization reaction is broad in scope and provides easy access to not only fused but also bridged bicyclic compounds.
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Enantiocontrolled Cyclization to Form Chiral 7- and 8-Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms.
J Am Chem Soc
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Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Chiral medium-sized rings, albeit displaying attractive properties for drug development, suffer from numerous synthetic challenges due to difficult cyclization steps that must take place to form these unusually strained, atropisomeric rings from sterically crowded precursors. In fact, catalytic enantioselective cyclization methods for the formation of chiral seven-membered rings are unknown, and the corresponding eight-membered variants are also sparse. In this work, we present a substrate preorganization-based, enantioselective, organocatalytic strategy to construct seven- and eight-membered rings featuring chirality that is intrinsic to the ring in the absence of singular stereogenic atoms or single bond axes of chirality.
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Natural and Medical Sciences Research Center (NMSRC), University of Nizwa Nizwa 616 Sulanate of Oman.
Diazo compounds are known to be good coupling partners in the synthesis of heterocycles, carbocycles and functionalized molecules a rhodium carbene-based strategy. Many heterocyclic and carbocyclic compounds, including isoquinolones and isocoumarins, quinoxalines, indoles, pyrrones, benzothazines, enaminones, benzenes and seven-membered rings, can be constructed using this rhodium-catalyzed system. The reaction mechanism involves C-H activation, carbene insertion and an annulation/functionalization sequence.
View Article and Find Full Text PDFConstruction of five- and seven-membered rings facilitated by alkyne-azide functionality: access to quinoline fused triazolo-azepines.
Org Biomol Chem
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Department of Chemistry, Central University of Punjab, Bathinda, Punjab, 151401, India.
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College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China.
Article Synopsis
- The paper discusses the challenges in creating axially chiral compounds using gold(I) catalysis, particularly in asymmetric synthesis, which has seen limited progress.
- A new method is introduced that utilizes gold/HNTf cocatalysis for asymmetric diazo-alkyne annulation, successfully producing chiral biaryls and arylquinones with high yields and enantioselectivity.
- The study also extends this methodology to synthesize seven-membered-ring atropisomers and includes insights about the mechanism and role of HNTf through computational and experimental analysis.
Ten-Step Total Synthesis of (±)-Phaeocaulisin A Enabled by Cyclopropanol Ring-Opening Carbonylation.
J Am Chem Soc
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Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.
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