Stereoselective Synthesis of a Bicyclic Ketooxetane <i>via</i> a Thionium Ion-Mediated Cyclisation Reaction

Craig, Donald C.; Lawrence, R. M.; Tapolczay, David J.

doi:10.1055/s-1997-949

Cited by 14 publications

(3 citation statements)

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“…The stereoselectivity was rationalized as resulting from minimization of unfavorable steric interactions between the bulky nucleophilic side chain and the ring system in the transition state. Extension of this methodology to more complex bicyclic systems from sugar derivatives was achieved by variation of the leaving group and cationic activator, either under the original conditions or with thiophenyl glycosides with tin chloride or ethylaluminium dichloride. , …”

Section: Synthesis Of Oxetane Derivatives By Intramolecular Cyclizationmentioning

confidence: 99%

“…Extension of this methodology to more complex bicyclic systems from sugar derivatives was achieved by variation of the leaving group and cationic activator, either under the original conditions or with thiophenyl glycosides with tin chloride or ethylaluminium dichloride. 231,232 Intramolecular cyclization with epoxide opening through C− C bond formation has been used to form oxetanes. First reported in 1976 by Still, 233 trans-epoxy allylic ether 173 was treated with sBuLi in THF/hexamethylphosphoramide (HMPA) at −78 °C to form vinyl oxetane 174 regioselectively, via stereospecific cyclization of the resulting allyloxycarbanion (Scheme 55).…”

Section: Cyclization Through C−c Bond Formationmentioning

confidence: 99%

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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: Synthesis Of Oxetane Derivatives By Intramolecular Cyclizationmentioning

confidence: 99%

Section: Cyclization Through C−c Bond Formationmentioning

confidence: 99%

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

et al. 2016

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“…In addition to being an analogue of the valued bicyclo[3.2.0]heptane skeleton, it might be expected to undergo interesting rearrangements that arise from the presence of both the protected tertiary alcohol and the strained oxetane ring. However, with the exception of a few analogues of more complex natural products, examples of 6‐oxabicyclo[3.2.0]heptanes with an oxygen function at the 1‐position are virtually unknown , …”

Section: Introductionmentioning

confidence: 99%

Stereoselective and Regioselective Pinacol‐Type Rearrangement of a Fused Bicyclic Oxetanol Scaffold

et al. 2017

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The Paternò‐Büchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to an unprecedented silyl ether derivative of 6‐oxabicyclo[3.2.0]heptan‐1‐ol. The bicyclic structure underwent selective reductive ring opening and acid‐catalyzed pinacol‐type rearrangement reactions with complete regioselectivity, accompanied by moderate to excellent mechanism‐dependent diastereoselectivity.

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