Parallel kinetic resolution of racemic aldehydes by use of asymmetric Horner-Wadsworth-Emmons reactions
[reaction: see text] A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.
Pedersen
TM
Department of Organic Chemistry, Technical University of Denmark, Kemitorvet, Kgs Lyngby.
Jensen
JF
Humble
RE
Rein
T
Tanner
D
Bodmann
K
Reiser
O