- Preparation of 2-Azabicyclo[21.1]hexane Hydrochloride
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A batchwise, multigram preparation of 2-azabicyclo-[2.1.1]hexane hydrochloride (1·HCl) was developed, delivering a total of 195 grams of material. The key synthetic step involves an intramolecular displacement of a primary alkyl chloride with a tert-butylsulfinamide to forge the [2.1.1]-bicyclic ring system.
- Liao, Haili,Li, Aimin,Chen, Xingsong,Liang, Kun,Shen, Yang,Liang, Qingfeng,Xu, Kewei,Shore, Daniel G. M.,Villemure, Elisia,Siu, Michael,Huestis, Malcolm P.
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- Confining the Χ space of basic natural amino acids: Cyclobutanederived Χ1, Χ2-constrained analogues of arginine, lysine and ornithine
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Four Χ1, Χ2-constrained cyclobutane-derived basic amino acidsdconformationally restricted analogues of arginine, lysine and ornithinedwere prepared as the derivatives properly protected for Fmoc-solid phase peptide synthesis. Compatibility of the synthesi
- Radchenko, Dmytro S.,Michurin, Oleg M.,Grygorenko, Oleksandr O.,Scheinpflug, Kathi,Dathe, Margitta,Komarov, Igor V.
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- Synthesis of 2,4-methanoproline analogues via an addition-Intramolecular substitution sequence
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A new two-step synthetic approach toward 3-(chloromethyl)cyclobutanone is described and used in the synthesis of 2,4-methanoproline analogues. The key step consists of a reversible addition of hydrogen cyanide onto the imines 12 in 50-74% yield under conditions that allow ring closure. 2-Alkyl-2-azabicyclo [2.1.1]hexane-1-carbonitriles 19, synthesized in four steps, can also be converted to the corresponding amines.
- Rammeloo, Thomas,Stevens, Christian V.,De Kimpe, Norbert
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p. 6509 - 6513
(2007/10/03)
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- A new entry into 2-azabicyclo[2.1.1]hexanes via 3-(chloromethyl)cyclobutanone
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2-Azabicyclo[2.1.1]hexanes, which possess the skeleton of 2,4-methanoproline (a naturally occurring insect antifeedant), were synthesized by imination of the previously unknown 3-(chloromethyl)cyclobutanone and subsequent reductive cyclization. The precursor of the latter, 3-oxocyclobutane carboxylic acid, was prepared by two pathways in multigram quantities.
- Stevens,De Kimpe
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p. 2174 - 2178
(2007/10/03)
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