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Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes
Author(s) -
Zhang Liangliang,
Oestreich Martin
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904272
Subject(s) - geminal , nucleophile , diastereomer , chemistry , catalysis , enantiomer , copper , silicon , medicinal chemistry , enantiomeric excess , stereochemistry , enantioselective synthesis , organic chemistry
Abstract 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.