Organocatalytic Synthesis of Α-Trifluoromethyl Allylboronic Acids by Enantioselective 1,2-Borotropic Migration
Journal of the American Chemical Society(2020)
摘要
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.
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关键词
Chiral Catalysts,Artificial Metalloenzymes,Asymmetric Synthesis,Trifluoromethylation
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