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Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.

Liangliang ZhangMartin Oestreich
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)
A highly stereocontrolled syn-addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper-catalyzed C-Si bond formation closes the gap of the direct synthesis of α-chiral cyclopropylsilanes.
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • transition metal