Strategies for the chemoenzymatic preparation of optically active 1-alkyn-3-ols.
A series of (R)- and (S)-1-alkyn-3-ols, chiral building units for the synthesis of leukotrienes and pheromones, were prepared via enantioselective hydrolysis of their racemic esters. While the majority of biocatalysts employed (lipases, fermenting or freeze-dried microorganisms) failed in discriminating between enantiomers, lyophilized cells of baker's yeast (Saccharomyces cerevisiae Hansen) gave (S)-1-alkyn-3-ols and their corresponding (R)-esters with greater than 90% e.e.
Glänzer
B I
BI
Institute of Organic Chemistry, Graz University of Technology, Austria.
Königsberger
K
K
Berger
B
B
Faber
K
K
Griengl
H
H
D000438:Alcohols / Q000138:chemical synthesis*; D000480:Alkynes / Q000138:chemical synthesis*; D001412:Bacillus subtilis; D001951:Brevibacterium; D055598:Chemical Phenomena; D002621:Chemistry; D004798:Enzymes; D008049:Lipase; D009904:Optical Rotation; D012233:Rhizopus; D012441:Saccharomyces cerevisiae
D000438:Alcohols; D000480:Alkynes; D004798:Enzymes; D008049:Lipase