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铑催化的芳基和烯基硼酸与α-亚甲基-β-内酰胺的共轭加成：反式-3,4-二取代β-内酰胺的立体选择性合成。

Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

机构信息

Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3060 United States.

出版信息

Org Lett. 2017 Sep 1;19(17):4460-4463. doi: 10.1021/acs.orglett.7b01994. Epub 2017 Aug 15.

DOI:10.1021/acs.orglett.7b01994
PMID:28809569
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5834916/
Abstract

A one-step preparation of 3,4-disubstituted β-lactones through Rh-catalyzed conjugate addition of aryl or alkenyl boronic acids to α-methylene-β-lactones is described. The operationally simple, stereoselective transformation provides a broad range of β-lactones from individual α-methylene-β-lactone templates. This methodology allowed for a direct, final-step C-3 diversification of nocardiolactone, an antimicrobial natural product.

摘要

通过 Rh 催化的芳基或烯基硼酸与α-亚甲基-β-内酰胺的共轭加成，一步制备 3,4-二取代的β-内酰胺。这种操作简单、立体选择性的转化提供了广泛的β-内酰胺，可从单个α-亚甲基-β-内酰胺模板中获得。该方法可直接实现诺卡内酯（一种抗菌天然产物）的 C-3 多样化的最后一步。

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