Enantiopure 1,5-diols from dynamic kinetic asymmetric transformation. Useful synthetic intermediates for the preparation of chiral heterocycles.
Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,5-diols has been performed in the presence of Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and ruthenium catalyst 4. The resulting optically pure 1,5-diacetates are useful synthetic intermediates, which was demonstrated by the syntheses of both an enantiopure 2,6-disubstituted piperidine and an enantiopure 3,5-disubstituted morpholine.
Leijondahl
Karin
K
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
Borén
Linnéa
L
Braun
Roland
R
Bäckvall
Jan-E
JE
D000438:Alcohols / Q000737:chemistry*; D016956:Burkholderia cepacia / Q000201:enzymology; D002384:Catalysis; D005656:Fungal Proteins; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D005656:Fungal Proteins; D006571:Heterocyclic Compounds; D012428:Ruthenium; D008049:Lipase; C431349:lipase B, Candida antarctica