Design and synthesis of novel C2-symmetric chiral piperazines and an application to asymmetric acylation of sigma-symmetric 1,2-diols.
[Structure: see text] A novel alicyclic chiral C2-symmetric piperazine, (S,S)-7, is designed and synthesized from L-proline. Benzoylation of a series of cyclic and acyclic meso-1,2-diols with a catalytic amount of (S,S)-7 and CuCl2 provided optically active monobenzoates with high enantioselectivity.
Nakamura
Daisuke
D
Research and Education Center for Materials Science and Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama, Ikoma-shi, Nara 630-0192, Japan.
Kakiuchi
Kiyomi
K
Koga
Kenji
K
Shirai
Ryuichi
R
D000215:Acylation; D015195:Drug Design; D010084:Oxidation-Reduction; D010879:Piperazines / Q000737:chemistry*; D013237:Stereoisomerism
D010879:Piperazines