Synthesis of 2-Azabicyclo[3.3.1]nonanes

Bonjoch, Josep; Diaba, Fai͏̈za; Bradshaw, Ben

doi:10.1055/s-0030-1258420

Cited by 48 publications

(19 citation statements)

References 97 publications

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“…This core subunit is found within over 300 natural products, including the strychnos, daphniphyllum, and madangamine families 1. Furthermore, it is present in many other biologically relevant molecules, such as the immunosuppressant FR901483, the cytotoxic agent aspernomine, and the analgesic morphine 1a…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Desymmetrization of Prochiral Cyclohexanones by Organocatalytic Intramolecular Michael Additions to α,β‐Unsaturated Esters

et al. 2015

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A new catalytic asymmetric desymmetrization reaction for the synthesis of enantioenriched derivatives of 2‐azabicyclo[3.3.1]nonane, a key motif common to many alkaloids, has been developed. Employing a cyclohexanediamine‐derived primary amine organocatalyst, a range of prochiral cyclohexanone derivatives possessing an α,β‐unsaturated ester moiety linked to the 4‐position afforded the bicyclic products, which possess three stereogenic centers, as single diastereoisomers in high enantioselectivity (83–99 % ee) and in good yields (60–90 %). Calculations revealed that stepwise CC bond formation and proton transfer via a chair‐shaped transition state dictate the exclusive endo selectivity and enabled the development of a highly enantioselective primary amine catalyst.

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Section: Methodsmentioning

confidence: 99%

Enantioselective Desymmetrization of Prochiral Cyclohexanones by Organocatalytic Intramolecular Michael Additions to α,β‐Unsaturated Esters

et al. 2015

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“…We envisioned that the highly functionalized 14‐membered ring would be formed at a later stage of the synthesis and the removal of the C9′–C18′ bridge would lead to the tetracyclic compound 2 , which is an equivalent of Overman’s intermediate 12. Cleavage of the NC bonds at N1C3′ and N1′C16, and further simplification generates the 2‐azabicyclo[3.3.1]nonane 3 13. The quaternary stereogenic center at C3 could be stereoselectively installed by means of the steric bias of the bicyclic system 14.…”

Section: Methodsmentioning

confidence: 99%

Formal Synthesis of Sarain A: Intramolecular Cycloaddition of an Eight‐Membered Cyclic Nitrone to Construct the 2‐Azabicyclo[3.3.1]nonane Framework

et al. 2015

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An enantioselective route to the tetracyclic skeleton of sarain Ah as been developed. Asymmetric reduction of an ynone introduced ac hiral center which was transferred to the contiguous tertiary stereogenic centers through an Ireland-Claisen rearrangement. The 2-azabicyclo[3.3.1]nonane framework was constructed by an unprecedented intramolecular cycloaddition of an eight-membered cyclic nitrone.U sing the steric bias of the bicyclic system, the quaternary carbon atom was constructed by astereoselective aldol reaction. Further ring formations were performed by ring-closing metathesis for the 13-membered ring and an iodoamidation reaction for the pyrrolidine ring. The present synthesis has successfully provided an alternative route to the late-stage intermediate of Overmans synthesis.

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“…6,7b,31 Our process also worked with alkynes as radical acceptors 32 (entry 6), yielding the corresponding g-lactam 21. The 6-exo-trig radical cyclisation of compounds 14-15 (entries 10-11) yielded morphans 25-27, thus constituting a new procedure to achieve this bridged azabicyclic scaffold 33 through a titanocene(III)-based methodology.…”

Section: Yieldmentioning

confidence: 99%

Synthesis of substituted γ- and δ-lactams based on titanocene(iii)-catalysed radical cyclisations of trichloroacetamides

et al. 2016

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Synthesis of 2-Azabicyclo[3.3.1]nonanes

Abstract: This review highlights advances in the synthesis of morphan compounds from 1980 to the present day.

Cited by 48 publications

References 97 publications

Enantioselective Desymmetrization of Prochiral Cyclohexanones by Organocatalytic Intramolecular Michael Additions to α,β‐Unsaturated Esters

Enantioselective Desymmetrization of Prochiral Cyclohexanones by Organocatalytic Intramolecular Michael Additions to α,β‐Unsaturated Esters

Formal Synthesis of Sarain A: Intramolecular Cycloaddition of an Eight‐Membered Cyclic Nitrone to Construct the 2‐Azabicyclo[3.3.1]nonane Framework

Synthesis of substituted γ- and δ-lactams based on titanocene(iii)-catalysed radical cyclisations of trichloroacetamides

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