Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 11, Pages 5788-5793Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202014127
Keywords
asymmetric catalysis; atropisomer; axial chirality; borinic acid; cooperative catalysis
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Funding
- NSFC [21871241, 92056102]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- China Postdoctoral Science Foundation [2019M662159]
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A Cu-catalyzed enantioselective ring-opening alkoxygenation reaction of cyclic diaryliodonium salts and diols was reported, with borinic acids playing a key role in selectively activating different types of diols. The proposed catalytic cycle involves a key ion pair model to account for the observed enantioselectivity. This study provides insights into the design of chiral catalysts for selective synthesis of cyclic molecules.
A Cu-catalyzed enantioselective ring-opening alkoxygenation reaction of cyclic diaryliodonium salts and diols in the presence of borinic acids was reported. Tuning structure of borinic acids with six or five-membered ring skeleton could selectively activate 1,2-diols or 1,4-diols. A catalytic cycle through a key ion pair model that accounts for the observed enantioselectivity was proposed.
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