Use of β‐Amido Allylboronate as a Nucleophilic Reagent in Catalytic Amide Allylation of N‐Carbonyl Imides. Issue 40 (30th October 2017)

• Record Type: Journal Article
• Authors: Sengoku, Tetsuya; Kamiya, Yuta; Kawakami, Ai; Takahashi, Masaki; Yoda, Hidemi
• Is Part Of: European journal of organic chemistry. Issue 40(2017)
• Page Start: 6096
• Page End: 6098
• Publication Date: 2017-10-30
• Subjects: Homogeneous catalysis -- Allylation -- Synthesis design; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701112
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : Application of the use of β‐amido allylboronate to the catalytic amide allylation of N ‐carbonyl imides is described. The boronates showed sufficient nucleophilicity toward imides in the presence of catalytic zinc bromide and basic additives, affording excellent yields of azaspiro‐γ‐lactones through a ring opening‐reclosure process on a gram scale.