期刊
ACS CENTRAL SCIENCE
卷 4, 期 5, 页码 656-660出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscentsci.8b00204
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资金
- Swiss National Science Foundation [BSSGI0-155902/1]
- University of Basel
- NCCR Molecular Systems Engineering
- Swiss National Science Foundation (SNF) [BSSGI0_155902] Funding Source: Swiss National Science Foundation (SNF)
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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