Mimicking dihydroxy acetone phosphate-utilizing aldolases through organocatalysis: a facile route to carbohydrates and aminosugars.
[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.
Suri
Jeff T
JT
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.
Ramachary
Dhevalapally B
DB
Barbas
Carlos F
CF
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
D000606:Amino Sugars; D002241:Carbohydrates; D000446:Aldehyde-Lyases