Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 31, Pages 8961-8965Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502569
Keywords
amino acids; arylation; chiral auxiliaries; enolates; pseudoephedrine
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Funding
- EPSRC
- Xunta de Galicia
- Syngenta (CASE)
- Royal Society
- EPSRC [EP/L018527/1, EP/L018527/2] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [1100862, EP/L018527/2, EP/L018527/1, 1331011] Funding Source: researchfish
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Available -amino acids undergo arylation at their position in an enantioselective manner on treatment with base of N-aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. Insitu silylation and enolization induces diastereoselective migration of the N-aryl group to the position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable auxiliary. The hydrolysis of the hydantoin products provides derivatives of quaternary amino acids. The arylation avoids the use of heavy-metal additives, and is successful with a range of amino acids and with aryl rings of varying electronic character.
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