De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy.
The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73-97% ee).
Ahmed
Md Moinuddin
MM
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Mortensen
Matthew S
MS
O'Doherty
George A
GA
D000438:Alcohols / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis*; D014867:Water / Q000737:chemistry
D000438:Alcohols; D004952:Esters; D014867:Water