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- Title
Geometry-Retentive C-Alkenylation of Lithiated α-Aminonitriles: Quaternary α-Alkenyl Amino Acids and Hydantoins.
- Authors
Mas ‐ Roselló, Josep; Hachisu, Shuji; Clayden, Jonathan
- Abstract
α-Amino nitriles tethered to alkenes through a urea linkage undergo intramolecular C-alkenylation on treatment with base by attack of the lithionitrile derivatives on the N′-alkenyl group. A geometry-retentive alkene shift affords stereospecifically the E or Z isomer of the 5-alkenyl-4-iminohydantoin products from the corresponding starting E- or Z- N′-alkenyl urea, each of which may be formed from the same N-allyl precursor by stereodivergent alkene isomerization. The reaction, formally a nucleophilic substitution at an sp2 carbon atom, allows the direct regioselective incorporation of mono-, di-, tri-, and tetrasubstituted olefins at the α-carbon of amino acid derivatives. The initially formed 5-alkenyl iminohydantoins may be hydrolyzed and oxidatively deprotected to yield hydantoins and unsaturated α-quaternary amino acids.
- Subjects
NITRILE derivatives; ALKENYLATION; AMINO acids; HYDANTOIN; ISOMERIZATION
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 36, p10890
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201704908