ChemInform Abstract: Cu(I)‐Catalyzed Oxidative Cyclization of Alkynyl Oxiranes and Oxetanes.

Gronnier, Colombe; Kramer, Soeren; Odabachian, Yann; Gagosz, Fabien

doi:10.1002/chin.201223033

Cited by 2 publications

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“…Alkynyloxetanes have been used in metal-catalyzed oxidative cyclization reactions. Gagosz and co-workers 548 showed that when alkynyloxetane 396 was treated with a Cu(I) catalyst in the presence of an oxidant, ring expansion occurred to form both dihydrofuran 397 and lactone 398 (Table 37). Careful tuning of the substituents on the pyridine N-oxide promoted selective formation of either product.…”

Section: Scheme 145 Enantioselective Synthesis Of Alternative Oxahete...mentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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Section: Scheme 145 Enantioselective Synthesis Of Alternative Oxahete...mentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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“…However, reducing catalyst loading to 1mol% led to as harp decrease of the yield (entry 17). Literature reportsr evealed that zinc [16] and copper [17] salts could also promote the oxygent ransfer reactionf rom pyridine N-oxides to alkynes. However, neither Zn(OTf) 2 nor Cu(OTf) 2 could catalyze this reaction(entries18and 19).…”

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confidence: 99%

One‐Pot Synthesis of 4‐Heteroaryl‐Substituted Pyrazoles: A Gold‐Catalyzed Oxidation/1,2‐Heteroaryl Migration Cascade Constitutes the Key Step

et al. 2016

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An efficient gold-catalyzed oxidation/1,2-heteroarylm igration cascade leading to 2-heteroaryl-substituted 1,3-diketones andi ts further application in the one-pot synthesis of 4-heteroaryl-substituted pyrazoles andt he preparation of 4-heteroarylsubstituted isoxazoles are reported. Aw ide variety of 4-heteroaryl-substituted pyrazoles were obtained, indicating the broad substrate scope and functional group tolerance of this method.

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ChemInform Abstract: Cu(I)‐Catalyzed Oxidative Cyclization of Alkynyl Oxiranes and Oxetanes.

Abstract: In the presence of a pyridine N‐oxide, the title reaction affords five‐ and six‐membered α,β‐unsaturated lactones.

Cited by 2 publications

References 1 publication

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

One‐Pot Synthesis of 4‐Heteroaryl‐Substituted Pyrazoles: A Gold‐Catalyzed Oxidation/1,2‐Heteroaryl Migration Cascade Constitutes the Key Step

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