Mimicking aldolases through organocatalysis: syn-selective aldol reactions with protected dihydroxyacetone.
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%.
Utsumi
Naoto
N
The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Imai
Masanori
M
Tanaka
Fujie
F
Ramasastry
S S V
SS
Barbas
Carlos F
CF
D000446:Aldehyde-Lyases; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004098:Dihydroxyacetone; D005634:Fructose-Bisphosphate Aldolase; D018716:Molecular Mimicry; D013237:Stereoisomerism; D013912:Threonine
D000447:Aldehydes; D013912:Threonine; C116609:3-hydroxybutanal; D000446:Aldehyde-Lyases; D005634:Fructose-Bisphosphate Aldolase; D004098:Dihydroxyacetone