Convergent Synthesis of Enantioenriched ortho-Fused Tricyclic Diketones via Catalytic Asymmetric Intramolecular Vinylogous Aldol Condensation.
Org Lett
; 24(49): 9017-9022, 2022 12 16.
Article
em En
| MEDLINE
| ID: mdl-36458918
ABSTRACT
Herein, we describe a catalytic asymmetric intramolecular vinylogous aldol reaction by taking advantage of dual organocatalysts, which enables convergent synthesis of ortho-fused tricyclic diketones in excellent enantioselectivities and diastereoselectivities. Noteworthy is that the reaction stereoselectively forges three consecutive stereogenic carbon centers including a quaternary one. Density functional theory calculations reveal that the enantioselectivity was facilitated by a transannular hydrogen bonding between the protonated quinuclidine moiety of the chiral aminocatalyst and the diketone fragment of the substrate.
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Base de dados:
MEDLINE
Assunto principal:
Aldeídos
/
Cetonas
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article