Organocatalytic Synthesis of α-Trifluoromethyl Allylboronic Acids by Enantioselective 1,2-Borotropic Migration.

ABSTRACT: Chiral α-substituted allylboronic acids were synthesized by asymmetric homologation of alkenylboronic acids using CF₃/TMS-diazomethanes in the presence of BINOL catalyst and ethanol. The chiral α-substituted allylboronic acids were reacted with aldehydes or oxidized to alcohols in situ with a high degree of chirality transfer. The oxygen-sensitive allylboronic acids can be purified via their isolated diaminonaphthalene (DanH)-protected derivatives. The highly reactive purified allylboronic acids reacted in a self-catalyzed reaction at room temperature with ketones, imines, and indoles to give congested trifluoromethylated homoallylic alcohols/amines with up to three contiguous stereocenters.

SUBMITTER: Jonker SJT 

PROVIDER: S-EPMC7760092 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature