Direct Synthesis of Previously Inaccessible Bridgehead Azabicyclics by Intramolecular Cyclization of α-Sulfonamido and α-Sulfonimido Radicals

Paquette, Leo A.; Sup, Choon; Schloss, Jeffrey D.; Leit, Silvana; Gallucci, Judith C.

doi:10.1021/jo010216z

Cited by 35 publications

(18 citation statements)

References 78 publications

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“…Despite these structural differences, all bridged sultams 392 were found to be hydrolytically stable. Using radical cyclization reaction, Paquette also reported the synthesis of bridged disulfonimide with a [3.2.2] ring system (Scheme 105), 438 and complex tricyclic bridged sultams. 439 The X-ray structure of 394 438 showed a large θ value ( 394 : θ = 345.8°; 392c : θ = 325.2°), indicating a relatively flexible sulfonimide bond in this compound.…”

Section: Synthesis Of Bridged Lactams With Complex Ring Systems Anmentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Synthesis Of Bridged Lactams With Complex Ring Systems Anmentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…In fact, lithiation of 3 with t BuLi was described by Paquette and co‐workers; the carbanion formed was used in the reaction with reactive alkylation reagents (i.e. allyl and benzyl bromides) . We have found that reaction of 3a–d with n BuLi in THF at –78 °C, followed by trapping of the organolithium species with carbon dioxide and acidic work‐up gave the target carboxylic acids 10a–d in 55–72 % yield.…”

Section: Resultsmentioning

confidence: 91%

“…Synthesis of the compound was previously reported by Paquette and colleagues by an alternative method …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalized Bridged Bicyclic Sulfonamides with a Bridgehead Nitrogen Atom

et al. 2020

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“…The importance of the sulfonamide function in the construction of the third and final ring of the molecule becomes fully apparent at this juncture. Deprotonation of 10 with t BuLi11 and capture of the anion with racemic octene oxide activated by BF 3 ⋅OEt 2 12 resulted in the formation of 11 , which was then subjected to a Dess–Martin oxidation13 to give 12 . A one‐pot sequence, which involved sequential β‐elimination and Miyaura borylation14 of the isolable intermediate 13 , resulted in the extremely rapid (20 min; the reaction normally requires >15 h) and highly diastereoselective15 formation of the boronic ester 14 (Scheme ).…”

Section: Methodsmentioning

confidence: 99%