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Abstract The enantioselective α‐functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6‐additions to para‐quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4‐ additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α‐functionalised α‐amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid‐based esters, amides or thioesters.