Aryl isoserines

Bartoli recently discovered that by switching from azide to p-anisidine as nucleophile, the ARO of racemic trans- 3-substituted styrene oxides could be catalyzed by the (salen)Cr-Cl complex 2 with complete regioselectivity and moderate selectivity factors (Scheme 7.36) [14]. The ability to access anti-P-amino alcohols nicely complements the existing methods for the preparation of syn-aryl isoserines and related compounds [67] by asymmetric oxidation of trans-cinnamate derivatives [68]. 

Palomo C, Aizpurua JM, Miranda JI, Mielgo A, Odriozola JM (1993) Asymmetric Synthesis of a-keto-/9-lactams via [2+2] Cycloaddition Reaction - A Concise Approach to Optically Active a-hydroxy /9-lactams and /9-alkyl(aryl)isoserines. Tetrahedron Lett 34 6325... 

Z. Guo, T. Shi, J. Jiang, L. Yang, W. Hu, Org. Biomol. Chem. 2009, 7, 5028-5033. Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H O and aryl imines a highly diastereoselective one-step synthesis of 3-aryl isoserine derivatives. 

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