Sigmatropic [1,5] Carbon Shift of Transient C3 Ammonium Enolates.
Angew Chem Int Ed Engl
; 61(31): e202204378, 2022 Aug 01.
Article
em En
| MEDLINE
| ID: mdl-35535567
ABSTRACT
The stereospecific sigmatropic [1,5] carbon shift of C3 ammonium enolates is discovered. According to mechanistic, kinetic and computational experiments, this new rearrangement proceeds via the catalytic generation of a transient C3 ammonium enolate by intramolecular aza-Michael addition. This intermediate rapidly undergoes [1,5] sigmatropic carbon migration to furnish the respective tetrahydroquinoline-4-ones with excellent diastereoselectivities of d.r. >99 1 and in 61-98 % yield.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article