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Catalyst-Controlled Stereodivergent Synthesis of Atropisomeric Multi-Axis Systems

Date Issued
2018-01-01
Author(s)
Lotter, Dominik  
Castrogiovanni, Alessandro  
Neuburger, Daniel  
Sparr, Christof  
DOI
10.1021/acscentsci.8b00204
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.
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