0000000000162748

AUTHOR

Johannes M. Wiest

showing 7 related works from this author

Recent Advances in Enantioselective Desymmetrizations of Prochiral Oxetanes

2021

Abstract Strain relief of oxetanes offers a plethora of opportunities for the synthesis of chiral alcohols and ethers. In this context, enantioselective desymmetrization has been identified as a powerful tool to construct molecular complexity and this has led to the development of elegant strategies on the basis of transition metal, Lewis acid, and Brønsted acid catalysis. This review highlights recent examples that harness the inherent reactivity of prochiral oxetanes and offers an outlook on the immense possibilities for synthetic application.

Molecular complexity010405 organic chemistryChemistryOrganic Chemistryoxetaneoxygen heterocyclesEnantioselective synthesisMinireviewsContext (language use)General ChemistryStrain relief010402 general chemistry01 natural sciencesCombinatorial chemistryDesymmetrizationCatalysis0104 chemical sciencesdesymmetrizationstrained moleculesMinireviewLewis acids and basesAsymmetric SynthesisChemistry – A European Journal
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Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ‐Lactams

2021

Abstract Asymmetric access to γ‐lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)‐1‐amino‐2‐indanol for chiral induction. Mechanistic analysis of the key N,O‐ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ‐lactams, including those bearing all‐carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further …

γ-lactamsChiral auxiliary010405 organic chemistryChemistryasymmetric synthesisEnantioselective synthesisCyclobutanoneGeneral Chemistry010402 general chemistryRing (chemistry)01 natural sciencesCombinatorial chemistryDesymmetrizationCatalysis0104 chemical sciencesStereocenterdesymmetrizationFormal synthesischemistry.chemical_compoundMoleculecyclobutanoneResearch ArticlesResearch ArticleAsymmetric Synthesis | Hot PaperAngewandte Chemie International Edition
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Desymmetrisierung von prochiralen Cyclobutanonen via Stickstoffinsertion: Ein einfacher Zugang zu chiralen γ‐Lactamen

2021

ChemistryGeneral MedicineAngewandte Chemie
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CCDC 2051971: Experimental Crystal Structure Determination

2021

Related Article: Jan Sietmann, Mike Ong, Christian Mück-Lichtenfeld, Constantin G. Daniliuc, Johannes M. Wiest|2021|Angew.Chem.,Int.Ed.|60|9719|doi:10.1002/anie.202100642

Space GroupCrystallographyCrystal SystemCrystal Structure1-(2-hydroxy-23-dihydro-1H-inden-1-yl)-4-phenylpyrrolidin-2-oneCell ParametersExperimental 3D Coordinates
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CCDC 2051973: Experimental Crystal Structure Determination

2021

Related Article: Jan Sietmann, Mike Ong, Christian Mück-Lichtenfeld, Constantin G. Daniliuc, Johannes M. Wiest|2021|Angew.Chem.,Int.Ed.|60|9719|doi:10.1002/anie.202100642

3-phenyl-3'3'a8'8'a-tetrahydrospiro[cyclobutane-12'-indeno[12-d][13]oxazole]Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 2051972: Experimental Crystal Structure Determination

2021

Related Article: Jan Sietmann, Mike Ong, Christian Mück-Lichtenfeld, Constantin G. Daniliuc, Johannes M. Wiest|2021|Angew.Chem.,Int.Ed.|60|9719|doi:10.1002/anie.202100642

Space GroupCrystallography1-(2-hydroxy-23-dihydro-1H-inden-1-yl)-4-methyl-4-phenylpyrrolidin-2-oneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 2051970: Experimental Crystal Structure Determination

2021

Related Article: Jan Sietmann, Mike Ong, Christian Mück-Lichtenfeld, Constantin G. Daniliuc, Johannes M. Wiest|2021|Angew.Chem.,Int.Ed.|60|9719|doi:10.1002/anie.202100642

Space GroupCrystallographyCrystal SystemCrystal Structure1-(2-hydroxy-23-dihydro-1H-inden-1-yl)-4-phenylpyrrolidin-2-oneCell ParametersExperimental 3D Coordinates
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