Abstract
An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An in situ generated ortho-boronic acid containing chalcone provides the chiral benzoxaboroles via an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excellent enantioselectivities (up to 99%) were obtained. The resulting benzoxaboroles were converted to the corresponding chiral β-hydroxy ketones without affecting the enantioselectivity.
Original language | English (US) |
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Pages (from-to) | 3026-3030 |
Number of pages | 5 |
Journal | Chemical Science |
Volume | 8 |
Issue number | 4 |
DOIs | |
State | Published - 2017 |
Externally published | Yes |
Bibliographical note
Publisher Copyright:© The Royal Society of Chemistry.