Premium
Use of β‐Amido Allylboronate as a Nucleophilic Reagent in Catalytic Amide Allylation of N ‐Carbonyl Imides
Author(s) -
Sengoku Tetsuya,
Kamiya Yuta,
Kawakami Ai,
Takahashi Masaki,
Yoda Hidemi
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701112
Subject(s) - chemistry , nucleophile , amide , imide , catalysis , reagent , potassium carbonate , organic chemistry , bromide , ether , medicinal chemistry , combinatorial chemistry
This communication describes the utility of β‐amido allylboronate as a nucleophile in the catalytic amide allylation of N ‐carbonyl imides. The reaction of the imide substrates with the boronates has been accomplished by using catalytic zinc bromide and basic additives (ethanol, potassium carbonate and 18‐crown 6‐ether), affording azaspiro‐γ‐lactones through a ring opening‐reclosure process with yields up to 100 %. The cost‐effective and easy‐to‐handle method established here tolerated for gram‐scale synthesis without significant loss of reaction efficiency.