ChemInform Abstract: Pseudoephedrine‐Directed Asymmetric α‐Arylation of α‐Amino Acid Derivatives.

Abstract

Pseudoephedrine-Directed Asymmetric -Arylation of -Amino Acid Derivatives. -Amino-acid-derived ureas (I) and (VI) are modified with pseudoephedrine as a chiral auxiliary to yield compounds (III) and (VII), which undergo LDA-promoted rearrangement including an aryl shift to yield hydantoins (IV) and (VIII). These hydantoins can be hydrolyzed to give chiral quaternary amino acids, e. g. compound (V). -(ATKINSON, R. C.; FERNANDEZ-NIETO, F.; MAS ROSELLO, J.; CLAYDEN*, J.; Angew. Chem., Int. Ed. 54 (2015) 31, 8961-8965, http://dx.doi.org/10.1002/anie.201502569 ; Sch. Chem., Univ. Manchester, Manchester M13 9PL, UK; Eng.) -Mais 49-127