Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 30, Pages 8723-8727Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201603153
Keywords
asymmetric catalysis; C-H activation; cyclopropanes; rhodium; silylation
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Funding
- NSF [GM-55382]
- NIH [S10-RR027172]
- Samsung Scholarship
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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 (S)-DTBM-SEGPHOS. The resulting enantioenriched oxasilolanes are suitable substrates for the Tamao-Fleming oxidation to form cyclopropanols with conservation of the ee 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.
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