title: Mimicking aldolases through organocatalysis: syn-selective aldol reactions with protected dihydroxyacetone.
abstract: A practical organocatalytic strategy designed to mimic the l-rhamnulose 1-phosphate and D-fructose 1,6-diphosphate aldolases has been developed and shown to be effective in the preparation of carbohydrates and polyol derivatives. Threonine-based catalysts facilitated the aldol reaction of protected dihydroxyacetone or protected hydroxacetone with a variety of aldehydes to provide syn-aldol products with good yields and ee's up to 98%.
authors.affiliation: The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Naoto
authors.initials: N
authors.lastname: Utsumi
authors.forename: Masanori
authors.initials: M
authors.lastname: Imai
authors.forename: Fujie
authors.initials: F
authors.lastname: Tanaka
authors.forename: S S V
authors.initials: SS
authors.lastname: Ramasastry
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000446:Aldehyde-Lyases; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004098:Dihydroxyacetone; D005634:Fructose-Bisphosphate Aldolase; D018716:Molecular Mimicry; D013237:Stereoisomerism; D013912:Threonine
chemical_list: D000447:Aldehydes; D013912:Threonine; C116609:3-hydroxybutanal; D000446:Aldehyde-Lyases; D005634:Fructose-Bisphosphate Aldolase; D004098:Dihydroxyacetone