Dynamic kinetic resolution of primary amines by a combined lipase-metal catalysis

ORGN 534

Lisa M. Kanupp, lisa@organ.su.se, Christine E. Hoben, Jens Paetzold, and Jan-E. Bäckvall. Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, SE-106 91 Stockholm, NA, Sweden
Kinetic resolution (KR) is used for the production of chiral compounds and entails the transformation of only one enantiomer in a racemic mixture into product. Two drawbacks of KR are that a maximum of half of the starting material can be utilized and that the product has to be separated from the remaining starting material. By using dynamic kinetic resolution (DKR), which entails racemiztion of the substrate, a 100% theoretical yield can be obtained. The principle has been used in our group for the DKR of alcohols. An efficient process for the DKR of amines was developed by our group via the combination of a ruthenium catalyst and a lipase, which provides the corresponding amides in high yields and high enantiomeric excess. Further investigations of this chemoenzymatic DKR of amines show that it is general and can be applied to various amines.