0000000001203491

AUTHOR

Jan Sietmann

showing 6 related works from this author

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
researchProduct

Desymmetrisierung von prochiralen Cyclobutanonen via Stickstoffinsertion: Ein einfacher Zugang zu chiralen γ‐Lactamen

2021

ChemistryGeneral MedicineAngewandte Chemie
researchProduct

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
researchProduct

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
researchProduct

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
researchProduct

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
researchProduct