Gold-Catalyzed Reactivity Reversal of Indolizidinone-Tethered β‑Amino Allenes Controlled by the Stereochemistry

The controllable cyclization reaction of indolizidinone-tethered β-amino allenes has been achieved through gold catalysis. The expected cycloisomerization of the syn-isomer sharply contrasts to the unprecedented bis­(azacyclization)–spirocyclization sequence of the epimeric anti-isomer, offering hig...

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Published inACS catalysis Vol. 5; no. 8; pp. 4842 - 4845
Main Authors Alcaide, Benito, Almendros, Pedro, Fernández, Israel, Martín-Montero, Raúl, Martínez-Peña, Francisco, Ruiz, M. Pilar, Torres, M. Rosario
Format Journal Article
LanguageEnglish
Published American Chemical Society 07.08.2015
Subjects
gold
selectivity
allenes
density functional calculations
heterocycles
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Summary:The controllable cyclization reaction of indolizidinone-tethered β-amino allenes has been achieved through gold catalysis. The expected cycloisomerization of the syn-isomer sharply contrasts to the unprecedented bis­(azacyclization)–spirocyclization sequence of the epimeric anti-isomer, offering highly selective access to enantiopure fused and spiranic azapolycycles.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.5b01061