4.7 Article

Copper(I)-catalyzed enantioselective hydroboration of cyclopropenes: facile synthesis of optically active cyclopropylboronates

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 1, Issue 9, Pages 1116-1122

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4qo00157e

Keywords

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Funding

  1. National Natural Science Foundation of China (NSFC) [21372243, 21232009, 21102161]
  2. Shanghai Municipal Committee of Science and Technology [13JC1406900]
  3. State Key Laboratory of Bioorganic and Natural Products Chemistry

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Copper(I)-catalyzed enantioselective hydroboration of 3-aryl substituted cyclopropene-3-carboxylate is described, providing chiral cyclopropylboronates with excellent enantioselectivities (89-95% ee) in moderate to high yields (55-86%). The non-directing effect of the ester group was observed, and the reaction proceeded with solely trans-selectivity. The chiral boronates could be conveniently converted into chiral 1,2-diaryl substituted cyclopropane derivatives.

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