Chemical Communications 2010-07-14

Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions.

Laurence Burroughs, Matthew E Vale, James A R Gilks, Henrietta Forintos, Christopher J Hayes, Paul A Clarke

Index: Chem. Commun. (Camb.) 46(26) , 4776-8, (2010)

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Abstract

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.