Iodide-Catalysed Cyclization of Unsaturated N-Chloroamines: A New Way to Synthesise 3-Chloropiperidines

Noack, Michael; Göttlich, Richard

doi:10.1002/1099-0690(200209)2002:18<3171::aid-ejoc3171>3.0.co;2-l

Cited by 54 publications

(53 citation statements)

References 11 publications

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“…12–16 The reactions can be catalyzed by Cu(I), 12,13,15 HOAc 14 and Bu 4 NI, 16 respectively. Electron-rich γ-unsaturated N -chloroamines underwent diastereoselective cyclization to form chloropiperidines under catalysis by CuCl (10 mol%) in THF at 50 °C.…”

Section: Regioselective and Diastereoselective Catalytic Alkene Ammentioning

confidence: 99%

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Metal Carbides as Alternative Electrocatalyst Supports

et al. 2013

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Catalytic aminohalogenation methods enable the regio- and stereoselective vicinal difunctionalization of alkynes, allenes and alkenes with amine and halogen moieties. A range of protocols and reaction mechanisms including organometallic, Lewis base, Lewis acid and Brønsted acid catalysis have been disclosed, enabling the regio- and stereoselective synthesis of halogen-functionalized acyclic amines and nitrogen heterocycles. Recent advances including aminofluorination and catalytic enantioselective aminohalogenation reactions are summarized in this review.

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Section: Regioselective and Diastereoselective Catalytic Alkene Ammentioning

confidence: 99%

“…Gottlich and co-workers subsequently found that N -chloropentamines can also undergo iodide-catalyzed 16 and Lewis-acid promoted 14 cyclizations, where more polar (non-radical) mechanisms are likely to be involved (Scheme 12). …”

Section: Regioselective and Diastereoselective Catalytic Alkene Ammentioning

confidence: 99%

Metal Carbides as Alternative Electrocatalyst Supports

et al. 2013

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“…[12][13][14][15][16] The reactions can be catalyzed by Cu(I), 12,13,15 HOAc 14 and Bu 4 NI, 16 respectively. Electron-rich γ-unsaturated N-chloroamines underwent diastereoselective cyclization to form chloropiperidines under catalysis by CuCl (10 mol%) in THF at 50 °C.…”

Section: Intramolecular Catalytic Aminohalogenation Of Electron-rich mentioning

confidence: 99%

“…13 Gottlich and co-workers subsequently found that N-chloropentamines can also undergo iodide-catalyzed 16 and Lewis-acid promoted 14 cyclizations, where more polar (non-radical) mechanisms are likely to be involved (Scheme 12).…”

Section: Intramolecular Catalytic Aminohalogenation Of Electron-rich mentioning

confidence: 99%

Catalytic Aminohalogenation of Alkenes and Alkynes

2013

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Catalytic aminohalogenation methods enable the regio-and stereoselective vicinal difunctionalization of alkynes, allenes and alkenes with amine and halogen moieties. A range of protocols and reaction mechanisms including organometallic, Lewis base, Lewis acid and Brønsted acid catalysis have been disclosed, enabling the regio-and stereoselective synthesis of halogen-functionalized acyclic amines and nitrogen heterocycles. Recent advances including aminofluorination and catalytic enantioselective aminohalogenation reactions are summarized in this review.

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“…[10] Our synthesis commenced with 1,5-dienoate 10 , prepared in large quantities (>100 g) over three steps from isobutyraldehyde (Scheme 2). [11] A large-scale (>60 g) ozonolysis of enoate 10 furnished aldehyde 11 in excellent yield. A Masamune-Roush modified Horner-Wadsworth-Emmons (HWE) olefination afforded enone 12 in good yield.…”

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confidence: 99%

A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products

et al. 2017

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The Armillaria and Lactarius genera of fungi produce antimicrobial and cytotoxic mellolide, protoilludane, and marasmane sesquiterpenoids. Herein, we report a unified synthetic strategy to access the protoilludane, mellolide, and marasmane families of natural products. The significance of these syntheses lies in a) the organocatalytic, enantioselective construction of key chiral intermediates from a simple achiral precursor, b) the utility of a key 1,2-butanediol intermediate to serve as a progenitor to each natural product class, and c) a direct chemical conversion of a protoilludane to a marasmane via serendipitous ring contraction, providing experimental support for their proposed biosynthetic relationships.

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Iodide-Catalysed Cyclization of Unsaturated N-Chloroamines: A New Way to Synthesise 3-Chloropiperidines

Cited by 54 publications

References 11 publications

Metal Carbides as Alternative Electrocatalyst Supports

Metal Carbides as Alternative Electrocatalyst Supports

Catalytic Aminohalogenation of Alkenes and Alkynes

A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products

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