Department of Chemistry, Faculty of Science , Hokkaido University , Kita 10 Nishi 8, Kita-ku , Sapporo , Hokkaido 060-0810 , Japan.
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) , Hokkaido University , Kita 21 Nishi 10, Kita-ku , Sapporo , Hokkaido 001-0021 , Japan.
Org Lett. 2019 Sep 20;21(18):7466-7469. doi: 10.1021/acs.orglett.9b02769. Epub 2019 Sep 5.
A boron-catalyzed α-amination of simple carboxylic acids was developed. Catalytically generated boron enolates of carboxylic acids reacted with an electrophilic aminating reagent, diisopropylazodicarboxylate, to provide amino acid derivatives. The catalysis afforded not only α-monosubstituted glycine derivatives but also α,α-disubstituted derivatives. The resulting α-aminocarboxylic acid was easily converted to carboxylic acid derivatives. Extension to a catalytic asymmetric variant was possible by introducing a chiral ligand on the boron catalyst.
发展了一种硼催化的简单羧酸的 α-胺化反应。羧酸的催化生成的硼烯醇盐与亲电的胺化试剂二异丙基重氮二甲酸酯反应，生成氨基酸衍生物。该催化反应不仅提供了 α-单取代的甘氨酸衍生物，还提供了 α,α-二取代的衍生物。所得的 α-氨基羧酸很容易转化为羧酸衍生物。通过在硼催化剂上引入手性配体，可以将其扩展到催化不对称变体。
