Molecular Catalyst Research Center, Chubu University , 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan.
J Am Chem Soc. 2016 Nov 2;138(43):14218-14221. doi: 10.1021/jacs.6b09482. Epub 2016 Oct 21.
We describe herein a new strategy for the chemoselective synthesis of amides by using a metal-catalyzed hydroxy-directed reaction. A hydroxy group located at the β-position of an ester group promoted the activation of a carbonyl group with a tantalum alkoxide catalyst followed by amidation reactions, leading to a wide variety of β-hydroxyamides with excellent chemeselectivity. The chemoselective amidation strategy can be extended to the catalytic synthesis of dipeptide derivatives, which remains challenging research subjects in modern organic synthesis.
我们在此描述了一种通过使用金属催化的羟基导向反应来实现酰胺的化学选择性合成的新策略。位于酯基β位的羟基促进了羰基与钽醇盐催化剂的活化，随后发生酰胺化反应，从而得到具有优异化学选择性的各种β-羟基酰胺。这种化学选择性的酰胺化策略可以扩展到二肽衍生物的催化合成，这在现代有机合成中仍是一个具有挑战性的研究课题。
