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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Aug 29

PMID 31457610

Citations 3

Authors

Eider Aranzamendi

Nuria Sotomayor

Esther Lete

Affiliations

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Abstract

An organolithium addition-intramolecular α-amidoalkylation sequence on -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 -triflylphosphoramides as catalysts are determinants to achieve reasonable levels of enantioselection, that is, up to 75% enantiomeric excess, in the α-amidoalkylation step. The procedure is complementary to the intermolecular α-amidoalkylation process, as opposite enantiomers are formed, and to the Pictet-Spengler cyclization, which allows the formation of tertiary stereocenters.

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