Rhodium‐Catalyzed Enantioselective Silylation of Cyclopropyl C−H Bonds
-
- Taegyo Lee
- Department of Chemistry University of California Berkeley CA 94720 USA
-
- John F. Hartwig
- Department of Chemistry University of California Berkeley CA 94720 USA
この論文をさがす
説明
<jats:title>Abstract</jats:title><jats:p>Hydrosilyl ethers, generated in situ by the dehydrogenative silylation of cyclopropylmethanols with diethylsilane, undergo asymmetric, intramolecular silylation of cyclopropyl C−H bonds in high yields and with high enantiomeric excesses in the presence of a rhodium catalyst derived from a rhodium precursor and the bisphosphine (<jats:italic>S</jats:italic>)‐DTBM‐SEGPHOS. The resulting enantioenriched oxasilolanes are suitable substrates for the Tamao–Fleming oxidation to form cyclopropanols with conservation of the <jats:italic>ee</jats:italic> value from the C−H silylation. Preliminary mechanistic data suggest that C−H cleavage is likely to be the turnover‐limiting and enantioselectivity‐determining step.</jats:p>
収録刊行物
-
- Angewandte Chemie
-
Angewandte Chemie 128 (30), 8865-8869, 2016-06
Wiley