Notes-Synthesis of 1-Methyl-1-azaspiro[5.5]-undecan-5-one

Schipper, Edgar; Chinery, Edwin

doi:10.1021/jo01068a619

Cited by 7 publications

(2 citation statements)

References 3 publications

(4 reference statements)

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“…A suspension of potassium carbonate (0.69 g, 5 mmol) in acetonitrile (10 mL) containing compound 9 (0.52 g, 2 mmol), potassium iodide (33 mg, 0.2 mmol), and benzyl bromide (0.47 mL, 4 mmol) was heated at 80 °C for 24 h. After cooling to ambient temperature, acetonitrile was evaporated, and the residue was taken up in diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure.…”

Section: Methodsmentioning

confidence: 92%

Aza-[2,3]-Wittig Sigmatropic Rearrangement of Allylic Tertiary Amines: A Successful Example with High Chirality Transfer

et al. 2015

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Section: Methodsmentioning

confidence: 92%

Aza-[2,3]-Wittig Sigmatropic Rearrangement of Allylic Tertiary Amines: A Successful Example with High Chirality Transfer

et al. 2015

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“…The first of these, carried out by the Schipper group in the 1960s, generated spirocycle 276 by Dieckmann condensation of tertiary amine 275, followed by decarboxylation (Scheme 31). 45 Unfortunately, this precursor lacks any of the substitution required in order to successfully convert it into the HTX skeleton, as well as presenting the problem of demethylating the nitrogen function. Later, in 1999, Tanner et al developed a formal synthesis of (±)-pHTX 16, utilising a [2,3]-sigmatropic rearrangement and ringclosing metathesis strategy (Scheme 32).…”

Section: Approach C: Formation Of the C2-c3 C3-cor C4-c5 Bondmentioning

confidence: 99%

Thirty-five years of synthetic studies directed towards the histrionicotoxin family of alkaloids

Sinclair

Stockman

2007

Nat. Prod. Rep.

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This article brings together for the first time reviews of all the synthetic attempts towards the spirocyclic histrionicotoxin alkaloids published since the discovery of the group in 1971. This covers 5 total syntheses of the fully unsaturated parent alkaloid HTX-283A, 7 total syntheses of perhydrohistrionicotoxin, 15 total syntheses of other members of this alkaloid family, 25 formal syntheses, and 19 partial syntheses involving the successful formation of the core azaspirocyclic structure but lacking advancement towards the target structure.

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Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution of Tetra‐substituted Morpholinone and Benzoxazinone Lactols

Zhu,

Manchado,

Omar Farah

et al. 2024

Angewandte Chemie

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The development of methods to allow the selective acylative dynamic kinetic resolution (DKR) of tetra‐substituted lactols is a recognised synthetic challenge. In this manuscript, a highly enantioselective isothiourea‐catalysed acylative DKR of tetra‐substituted morpholinone and benzoxazinone‐derived lactols is reported. The scope and limitations of this methodology have been developed, with high enantioselectivity and good to excellent yields (up to 89%, 99:1 er) observed across a broad range of substrate derivatives incorporating substitution at N(4) and C(2), di‐ and spirocyclic substitution at C(5)‐ and C(6)‐position, as well as benzannulation (>35 examples in total). The DKR process is amenable to scale‐up on a 1 g laboratory scale. The factors leading to high selectivity in this DKR process have been probed through computation, with an N‐C=O•••isothiouronium interaction identified as key to producing ester products in highly enantioenriched form.

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Notes-Synthesis of 1-Methyl-1-azaspiro[5.5]-undecan-5-one

Cited by 7 publications

References 3 publications

Aza-[2,3]-Wittig Sigmatropic Rearrangement of Allylic Tertiary Amines: A Successful Example with High Chirality Transfer

Aza-[2,3]-Wittig Sigmatropic Rearrangement of Allylic Tertiary Amines: A Successful Example with High Chirality Transfer

Thirty-five years of synthetic studies directed towards the histrionicotoxin family of alkaloids

Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution of Tetra‐substituted Morpholinone and Benzoxazinone Lactols

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