Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditionsElectronic supplementary information (ESI) available: Experimental procedures and compound characterisation data. See DOI: 10.1039/c0cc00613k

Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under aqueous conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of ( l )-proline yield ( l )-carbohydrates, esters of ( l )-leucine and ( l )-alanine generate ( d )-carbohydrates, offering the potential to account for the prebiotic link between natural ( l )-amino acids and natural ( d )-sugars. Amino acid esters efficiently catalyse the formation of simple carbohydrates under aqueous conditions. Esters of ( l )-leucine and ( l )-alanine generate ( d )-carbohydrates, offering the potential to account for the link between natural ( l )-amino acids and natural ( d )-sugars.