biostudies-literatureUnknown8(4)Hazra GAn unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An <i>in situ</i> generated <i>ortho</i>-boronic acid containing chalcone provides the chiral benzoxaboroles <i>via</i> 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.Chemical science3026-3030https://www.ebi.ac.uk/biostudies/studies/S-EPMC5380879biostudies-literatureOrganocatalytic, enantioselective synthesis of benzoxaboroles <i>via</i> Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids.PMC5380879Hazra GGhorai PMaity SBhowmick SfalseOrganocatalytic, enantioselective synthesis of benzoxaboroles <i>via</i> Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids.An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An <i>in situ</i> generated <i>ortho</i>-boronic acid containing chalcone provides the chiral benzoxaboroles <i>via</i> 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.2017-01-01T00:00:00Z2017 Apr2026-05-05T09:49:16.847Z2019-03-27T02:40:23ZS-EPMC53808792845137010.1039/c6sc04522g