Asymmetric Petasis reaction for the synthesis of chiral α- and ß-butadienyl amines.
Chem Commun (Camb)
; 57(19): 2364-2367, 2021 Mar 07.
Article
en En
| MEDLINE
| ID: mdl-33533779
ABSTRACT
The Petasis reaction using (1S,2R)-1-amino-2-indanol as the substrate and an activator to construct α- and ß-butadienyl amines in optically pure forms was realized, which are otherwise difficult to prepare. The reactions feature a metal-free nature, broad substrate scope, complete regioselectivities (γ-selectivity of pinacol homoallenyl- and isoprenylboronates), and high to excellent chirality induction (up to >20 1 dr). The favored nucleophilic addition across the Si-face of the imine intermediate was explained using DFT calculations of the six-membered chair-like transition state.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Chem Commun (Camb)
Asunto de la revista:
QUIMICA
Año:
2021
Tipo del documento:
Article
País de afiliación:
China