Unknown

Dataset Information

0

Phenolic Activation in Chiral Bronsted Acid-Catalyzed Intramolecular ?-Amidoalkylation Reactions for the Synthesis of Fused Isoquinolines.


ABSTRACT: An organolithium addition-intramolecular ?-amidoalkylation sequence on N-phenethylimides has been developed for the synthesis of fused tetrahydroisoquinoline systems using 1,1'-bi-2-naphthol (binol)-derived Brønsted acids. This transformation is the first in which activated benzene derivatives are used as internal nucleophiles, instead of electron-rich heteroaromatics, generating a quaternary stereocenter. Phenolic substitution on the aromatic ring of the phenethylamino moiety and the use of binol-derived N-triflylphosphoramides as catalysts are determinants to achieve reasonable levels of enantioselection, that is, up to 75% enantiomeric excess, in the ?-amidoalkylation step. The procedure is complementary to the intermolecular ?-amidoalkylation process, as opposite enantiomers are formed, and to the Pictet-Spengler cyclization, which allows the formation of tertiary stereocenters.

SUBMITTER: Aranzamendi E 

PROVIDER: S-EPMC6641169 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

altmetric image

Publications

Phenolic Activation in Chiral Brønsted Acid-Catalyzed Intramolecular α-Amidoalkylation Reactions for the Synthesis of Fused Isoquinolines.

Aranzamendi Eider E   Sotomayor Nuria N   Lete Esther E  

ACS omega 20170616 6


An organolithium addition-intramolecular α-amidoalkylation sequence on <i>N</i>-phenethylimides has been developed for the synthesis of fused tetrahydroisoquinoline systems using 1,1'-bi-2-naphthol (binol)-derived Brønsted acids. This transformation is the first in which activated benzene derivatives are used as internal nucleophiles, instead of electron-rich heteroaromatics, generating a quaternary stereocenter. Phenolic substitution on the aromatic ring of the phenethylamino moiety and the use  ...[more]

Similar Datasets

| S-EPMC5167290 | biostudies-literature
| S-EPMC10017053 | biostudies-literature
| S-EPMC3474359 | biostudies-literature
| S-EPMC9089239 | biostudies-literature
| S-EPMC8117943 | biostudies-literature
| S-EPMC3519432 | biostudies-literature
| S-EPMC9435037 | biostudies-literature
| S-EPMC2928988 | biostudies-literature
| S-EPMC5502890 | biostudies-literature