title: Mimicking dihydroxy acetone phosphate-utilizing aldolases through organocatalysis: a facile route to carbohydrates and aminosugars.
abstract: [reaction: see text] A practical and environmentally friendly organocatalytic strategy designed to mimic the DHAP aldolases has been developed and shown to be effective in the preparation of carbohydrates and aminosugars. (S)-Proline and (S)-2-pyrrolidine-tetrazole catalyzed the aldol reaction between dihydroxy acetone variants such as 1,3-dioxan-5-one and 2,2-dimethyl-1,3-dioxan-5-one with aldehydes to give the corresponding polyols in good yields with very high ees.
authors.affiliation: The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Jeff T
authors.initials: JT
authors.lastname: Suri
authors.forename: Dhevalapally B
authors.initials: DB
authors.lastname: Ramachary
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000446:Aldehyde-Lyases / Q000737:chemistry / Q000378:metabolism*; D000606:Amino Sugars / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000138:chemical synthesis*; D002384:Catalysis; D018716:Molecular Mimicry; D015394:Molecular Structure
chemical_list: D000606:Amino Sugars; D002241:Carbohydrates; D000446:Aldehyde-Lyases