Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 1, Pages 68-72Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200782
Keywords
asymmetric organocatalysis; bifunctional catalysts; boron tethers; bromohydroxylation; regioselectivity
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Funding
- Chinese Academy of Sciences
- National Natural Science Foundation of China [21202187, 20921091]
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The asymmetric bromohydroxylation of 2-aryl-2-propen-1-ols catalyzed by quinine-derived bifunctional catalyst has been developed. The regioselectivity was controlled by employing a boronate ester as tether which was formed in situ and enantioselectivity was introduced by taking advantage of a quinine-derived bifunctional catalyst which activated the boronate ester and N-bromosuccinimide (NBS) at the same time. Chiral bromohydrin, which is a useful feedstock in organic synthesis, was produced in moderate to excellent enantioselectivity in a two-step reaction sequence.
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