Enzyme- and ruthenium-catalyzed dynamic kinetic resolution of functionalized cyclic allylic alcohols.
Enantioselective synthesis of functionalized cyclic allylic alcohols via dynamic kinetic resolution has been developed. Cyclopentadienylruthenium catalysts were used for the racemization, and lipase PS-IM or CALB was employed for the resolution. By optimization of the reaction conditions the formation of the enone byproduct was minimized, making it possible to prepare a range of optically active functionalized allylic alcohols in good yields and high ee's.
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University , SE-106 91 Stockholm, Sweden.
Richard
R
Lihammar
Renaud
R
Millet
Jan-E
JE
Bäckvall
D002384:Catalysis; D007700:Kinetics; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D012428:Ruthenium / Q000737:chemistry* / Q000378:metabolism
D020005:Propanols; C006463:allyl alcohol; D012428:Ruthenium; D008049:Lipase