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Synthesis 2018; 50(05): 1166-1174
DOI: 10.1055/s-0036-1589131
DOI: 10.1055/s-0036-1589131
paper
Catalytic Direct Nucleophilic Substitution of Primary Morita–Baylis–Hillman Adducts and Application to the Straightforward Synthesis of Dihydroisoindolones
Further Information
Publication History
Received: 15 September 2017
Accepted after revision: 17 October 2017
Publication Date:
14 November 2017 (online)
Abstract
An interesting γ-carbonyl effect permits the dual iron/boron-catalyzed direct nucleophilic substitution of functionalized primary allylic alcohols with a large variety of nucleophiles. The resulting substitution products are useful synthetic platforms for heterocycle synthesis, as illustrated in a ready access to tetrahydroisoindol-4-ones.
Key words
iron catalysis - boron catalysis - dual catalysis - isoindolones - nucleophilic substitution - neighboring group participationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589131.
- Supporting Information
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For the synthesis of cyclic MBH adducts see:
For the synthesis of acyclic MBH adducts see: