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Catalyst-Controlled Stereodivergent Synthesis of Atropisomeric Multiaxis Systems.

ABSTRACT: Molecular scaffolds with multiple rotationally restricted bonds allow a precise spatial positioning of functional groups. However, their synthesis requires methods addressing the configuration of each stereogenic axis. We report here a catalyst-stereocontrolled synthesis of atropisomeric multiaxis systems enabling divergence from the prevailing stereochemical reaction path. By using ion-pairing catalysts in arene-forming aldol condensations, a strong substrate-induced stereopreference can be overcome to provide structurally well-defined helical oligo-1,2-naphthylenes. The configuration of up to four stereogenic axes was individually catalyst-controlled, affording quinquenaphthalenes with a unique topology.

SUBMITTER: Lotter D

PROVIDER: S-EPMC5968508 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Catalyst-Controlled Stereodivergent Synthesis of Atropisomeric Multiaxis Systems.

Lotter Dominik D Castrogiovanni Alessandro A Neuburger Markus M Sparr Christof C

ACS central science 20180509 5

Molecular scaffolds with multiple rotationally restricted bonds allow a precise spatial positioning of functional groups. However, their synthesis requires methods addressing the configuration of each stereogenic axis. We report here a catalyst-stereocontrolled synthesis of atropisomeric multiaxis systems enabling divergence from the prevailing stereochemical reaction path. By using ion-pairing catalysts in arene-forming aldol condensations, a strong substrate-induced stereopreference can be ove ...[more]

PMID: 29806013

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