Highly efficient synthesis of enantiopure diacetylated C(2)-symmetric diols by ruthenium- and enzyme-catalyzed dynamic kinetic asymmetric transformation (DYKAT).
Highly efficient synthesis of enantiopure diacetates of 2,4-pentanediol and 2,5-hexanediol starting from commercially available mixtures of the diols (dl/meso approximately 1:1) has been realized by combining a fast ruthenium-catalyzed epimerization with an enzymatic transesterification. The in situ coupling of these two processes produces the diacetates in high yield in >99 % enantiomeric excess.
Martín-Matute
Belén
B
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden.
Edin
Michaela
M
Bäckvall
Jan-E
JE
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D006018:Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D006018:Glycols; D009942:Organometallic Compounds; C007938:2,5-hexanediol; C065140:2,4-pentanediol; D012428:Ruthenium; D008049:Lipase