Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 41, Pages 11041-11045Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406192
Keywords
acylation; axial chirality; enantioselectivity; kinetic resolution; N-heterocyclic carbene
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Funding
- Singapore National Research Foundation (NRF Fellowship)
- National University of Singapore
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We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1'-biaryl-2,2'-diols and amino alcohols to provide them in uniformly >99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.
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